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CHED Abstracts

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CHED 1 Green chemistry: Connections to our world Kate Anderson, [email protected], Mollie Enright. Beyond Benign, Wilmington, Massachusetts, United States The Next Generation Science Standards call for students to analyze problems and create solutions. Green chemistry is the science of creating safe, energy efficient and non-toxic processes and products that provide sustainable solutions for the environmental problems facing our society today. Green chemistry provides a framework and lens for learning, teaching and investigating chemistry concepts. Highlighting industrial examples of sustainable design is one way to engage students and provide an opportunity to demonstrate how chemistry connects to our world. Learn how innovative green chemistry technologies are serving as tools to capture the imagination of the next generation of problem solvers. Teachers and students alike, delight in the interactive and engaging activities that bring these innovative ideas, designs and applications to life. CHED 2 Developing a high school organic chemistry course Esther Hines, des_hin[email protected]. Science, Billerica Memorial High School, Billerica, Massachusetts, United States Developing an Organic Chemistry Course at Billerica Memorial High School Esther Hines, Billerica Memorial High School, Billerica MA [email protected] The high school organic chemistry course taught at Billerica Memorial High School, Billerica MA, was offered for the first time in the Fall of 2014. This course is open to all students as a semester elective. The students who selected this course in the past two years have been interested in pursuing careers in the medical and or health fields after high school. The lecture portion of the course starts with a vocabulary lesson in which the familiar terms used in general chemistry is “translated to organic chemistry language”, a practice that continuous throughout the follow up units. We have adopted a textbook, purchased with a generous donation from a local company. The course has a laboratory section component. The selection of laboratory experiments we used was determined by the laboratory infrastructure at our high school, the budget (both from our STEM department and grants), and the topics of interest by the students (based on surveyed results). I will share our course curriculum, laboratory experiments we currently do, sources from which we obtained our lab kits, and the inclusion of green chemistry experiments in the course.
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Green chemistry: Connections to our world

Kate Anderson, [email protected], Mollie Enright. Beyond Benign, Wilmington, Massachusetts, United States

The Next Generation Science Standards call for students to analyze problems and create solutions. Green chemistry is the science of creating safe, energy efficient and non-toxic processes and products that provide sustainable solutions for the environmental problems facing our society today. Green chemistry provides a framework and lens for learning, teaching and investigating chemistry concepts. Highlighting industrial examples of sustainable design is one way to engage students and provide an opportunity to demonstrate how chemistry connects to our world. Learn how innovative green chemistry technologies are serving as tools to capture the imagination of the next generation of problem solvers. Teachers and students alike, delight in the interactive and engaging activities that bring these innovative ideas, designs and applications to life.


Developing a high school organic chemistry course

Esther Hines, [email protected]. Science, Billerica Memorial High School, Billerica, Massachusetts, United States

Developing an Organic Chemistry Course at Billerica Memorial High School Esther Hines, Billerica Memorial High School, Billerica MA [email protected] The high school organic chemistry course taught at Billerica Memorial High School, Billerica MA, was offered for the first time in the Fall of 2014. This course is open to all students as a semester elective. The students who selected this course in the past two years have been interested in pursuing careers in the medical and or health fields after high school. The lecture portion of the course starts with a vocabulary lesson in which the familiar terms used in general chemistry is “translated to organic chemistry language”, a practice that continuous throughout the follow up units. We have adopted a textbook, purchased with a generous donation from a local company. The course has a laboratory section component. The selection of laboratory experiments we used was determined by the laboratory infrastructure at our high school, the budget (both from our STEM department and grants), and the topics of interest by the students (based on surveyed results). I will share our course curriculum, laboratory experiments we currently do, sources from which we obtained our lab kits, and the inclusion of green chemistry experiments in the course.

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We look forward to your input to guide our efforts with this course since it is a work in progress.


Atoms, molecules, and ions – Oh my! Teacher-designed inquiry activities with particulate models

Ellen J. Yezierski2, [email protected], Deborah G. Herrington1. (1) Dept of Chem, Grand Valley State University, Allendale, Michigan, United States (2) Chemistry & Biochemistry, Miami University, Oxford, Ohio, United States

This session features classroom-ready, teacher-developed, and teacher-tested inquiry activities with a focus on particulate level models and building conceptual understanding. Participants will interact with the activities developed by high school chemistry teachers who completed the nationally known professional development program, Target Inquiry at Miami University. Participants will also discuss important considerations for facilitating the activities as well as strategies for incorporating more inquiry into their own lessons. Topics include stoichiometry, intermolecular forces, and redox, to name a few. Participants will be introduced to the Target Inquiry web sites at Miami University and Grand Valley State University where they can join over 3,000 teachers across the world who have accessed Target Inquiry student and teacher guides.


Advancing scientific literacy with inquiry based lessons designed around ChemMatters articles

Kathy Chesmel, [email protected]. Science, New Egypt High School, Cream Ridge, New Jersey, United States

Science teachers are being asked to incorporate additional and rigorous reading and writing tasks into their lessons to support literacy in the science classroom. The goal of these tasks is to help students think critically as they use informational texts to deepen their understanding of the nature of science and important scientific concepts. One way of weaving instruction in reading, writing and speaking into chemistry content is using challenging, grade-level appropriate articles that examine the exciting science behind everyday life. In this workshop, specific strategies to improve students’ understanding of scientific concepts through reading and conducting their own investigations will be explored. Some of the most highly ranked ChemMatters articles will be used as exemplars to demonstrate the process of developing and implementating inquiry lesson plans based on non-fiction texts. Strategies to create specific learning goals and authentic

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assessments that are in line with Next Generation Science Standards and Common Core State Standards will be discussed. Assessments include presentations, debates, and other creative projects that stimulate student interest, develop content knowledge and expand scientific literacy. In the second part of the workshop participants will engage in building their own lesson plans designed to teach high-level literacy skills and promote critical and analytical thinking. To assist with this activity, we will provide a selection of ChemMatters articles, templates for building lessons, and relevant sections of the ChemMatters Teacher Guide. After the workshop the lesson plans will be refined, formatted and posted on the ACS website for use in the classrooms.


Student centered activities from JCE & ChemEd X

Deanna Cullen, [email protected]. Chemistry, Whitehall High School , Montague, Michigan, United States

The Journal of Chemical Education has been a reliable source for research-based activities for over nine decades. ChemEd X provides an interactive venue for collaboration that helps bridge the gap between the research and introductory chemistry courses at the high school and college level courses. Engage in student-centered activities from both sources.


Ötzi the iceman meets the new IUPAC periodic table of the elements and isotopes

Peter G. Mahaffy1,2, [email protected], Brian Martin2, Mckenzie Oliver2, Tyler DeBoon2. (1) Chemistry, The King's University, Edmonton, Alberta, Canada (2) King's Centre for Visualization in Science, Edmonton, Alberta, Canada

A hand goes up in your chemistry classroom. “What is the atomic weight of hydrogen?” It used to be 1.0079, a number that I can plug into calculating molar mass values. But on the new periodic table it is shown as [1.007 , 1.009], an interval between two numbers! Enter Ötzi the well-preserved 5,300 year old frozen mummy found on a melting glacier in the Ötztal Alps along the Austrian-Italian border. Ötzi serves as an entry point for teachers and students to an IUPAC project to create for the education community an interactive, electronic version of the IUPAC Periodic Table of the Elements and Isotopes. The electronic resources will be formally launched for global dissemination in August at the ACS National Meeting in Philadelphia and the International Conference on Chemistry Education in Malaysia. Data about Ötzi’s Pb, Sr and O isotopes helped forensic scientists determine where he lived as a child and an adult.

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The IUPAC Periodic Table of the Elements and Isotopes has been created to familiarize students, teachers, and the public with the existence and importance of isotopes of the chemical elements. For some elements like Hydrogen, the atomic weight is no longer considered to be a constant of nature, since the ratios of the constituent isotopes can vary in nature. The new interactive, electronic version of the Periodic Table of the Elements and Isotopes, which has been created by the research team at the King’s Centre for Visualization in Science (www.kcvs.ca), will be presented in this session, and you will learn how you can make use of KCVS interactive digital learning objects and electronic resources to help your students wrap their minds around these important changes to the periodic table that hangs on your classroom wall. We will also explore how we can introduce students to the widespread importance of isotopic variability, with applications in medicine, forensics, and proxy measurements for climate. The new interval IUPAC atomic weights complicate life for plug-and-chug calculations for our students, but the variability of isotopic abundances also presents intriguing opportunities for rich and deep education about fundamental ideas related to atoms, isotopes, and atomic weights.


Total Synthesis of Pyrophen and Campyrones A-C

Hannah Burdge, [email protected]. Chemistry, Towson University, Towson, Maryland, United States

The total synthesis of the novel compounds pyrophen and campyrones A, B and C, isolated from the fungus Aspergillus niger, is reported for the first time. Beginning from L-phenylalanine, L-isoleucine, L-leucine and L-valine respectively, key steps in this route include a Claisen condensation utilizing N-acylbenzotriazoles to form a pivotal carbon-carbon bond and a dioxinone thermolysis/cyclization sequence to generate the α-pyrone moiety. These compounds have displayed promising antifungal activity against Candida albicans, and in partnership with Eli Lilly’s Open Innovation Drug Discovery (OIDD) program, we plan to examine the full potential of this biological activity.

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ORGN: Developing a synthetic route to caramboxin, a rare bioactive non-peptidic amino acid

Chris Fritschi, [email protected], Andrea Pascucci, Luis Sanchez. Niagara University, West Seneca, New York, United States

While safe for everyone else, ingestion of Averrhoa carambola, more commonly known as star fruit, can be harmful to chronic kidney disease patients; symptoms such as vomiting, mental confusion, and seizures and even deaths have been reported. Caramboxin has been recently identified as the active compound responsible for these effects and its molecular structure has been determined to be an amino acid-like moiety resembling phenylalanine. Our interest in caramboxin lies on its orsellinic acid-like aromatic ring, a feature present in a number of medically relevant natural products. These compounds and their analogues are currently being investigated for the treatment of malaria, menopause symptoms, and various forms of cancer. We envision that caramboxin, as an amino acid, has the potential to be incorporated in peptide-like compounds for the development of novel drugs. With this in mind, synthetic access to large quantities of this rare active amino acid for biological studies is highly desirable. Given that the chirality of caramboxin has not been determined, the present project aims at its first total synthesis for structural confirmation. Furthermore, our synthetic route, which begins with aspartic acid, may provide a glimpse at how this molecule is produced in nature by Averrhoa carambola.


ORGN: Tuning chemoselectivity toward an affordable synthesis of aurantioclavine

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Zachary Mariani, [email protected], Luis Sanchez. Niagara University, Wilson, New York, United States

Aurantioclavine is a natural product isolated from Penicillium aurantiovirens that gained the interest of the synthetic community for its proposed role in the biosynthesis of the complex polycylic alkaloids of the communesin family. Members of this family display notable bioactivities, including insecticidal properties and cytotoxicity toward leukemia cell lines. Our interest in this important compound lies in its structural resemblance to tryptamine, a derivative of the amino acid tryptophan. Since tryptamine is readily available and more than a hundred times less expensive than the starting materials used in the reported total syntheses of aurantioclavine, we aim at developing a rational reaction sequence to progressively transform tryptamine and access aurantioclavine synthetically. This approach, nevertheless, is bound to involve an “unfavored” cyclization in order to assemble aurantioclavine’s characteristic seven-membered ring. We expect to tune the chemical selectivity of this process via the functionalization of the indole ring and pendant chain of tryptamine—altering the geometry and electronics of the functionalities involved in the cyclization. Our progress in these efforts will be presented.


Ligand-driven pursuit of structure of d(CAGAGG)n repeats

Barrett Powell1, [email protected], Jessica Chen1, Eric Brown2, Liliya A. Yatsunyk1. (1) Chemistry and Biochemistry, Swarthmore College, Swarthmore, Pennsylvania, United States (2) Perelman School of Medicine, University of Pennsylvania, Philadelphia, Pennsylvania, United States

In the mouse genome, the repeats of (CAGAGG)n have been identified to be associated with collapse of replication forks. Such a collapse can potentially cause breakpoints leading to translocations and other types of mutations, contributing to cancer. The structure of (CAGAGG)n repeats is not known but previous biophysical studies from our lab led us to propose a model consisting of a quadruplex core built using canonical C-G base pairs, and possibly stabilized by noncanonical AG and GG base pairs in loops above and below the core structure. Recent crystallization efforts led to successful crystal formation, but with poor diffraction pattern with resolution of up to 6 Å. We therefore screened for small molecule ligands (NMM, TMPyP4, RHPS4, etc) known to bind to a variety of DNA structures that would stabilize the (CAGAGG)n repeat without altering its existing secondary structure. Binding of ligands was determined using UV-vis and CD titrations and their stabilizing ability was tested in CD melting studies. Ligands capable binding to, stabilizing, and not altering the structure of (CAGAGG)n were used for co-crystallization with (CAGAGG)n. Results of successful crystallization trials will be discussed. Biological implication of (CAGAGG)n secondary structure will be presented.


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Towards validation of novel Hepatitis C virus drug target via computer-aided molecular design

Aisha A. Alharbi , [email protected], Elaf A. Felemban , Ohoud I. Qadi, Anfal K. Bajammal, Abdelsattar M. Omar, Maan T. Khayat, Moustafa E. El-Araby. Pharmaceutical Chemistry Dept. , King Abdulaziz University, Faculty of Pharmacy , Jeddah , Saudi Arabia

Causing mild symptoms such as fever, fatigue, nausea and tenderness in the liver, Hepatitis C is a snarky disease that is as a sly as it is deadly. It causes terrible complications, from something as seemingly simple as liver scarring to cirrhosis to, irrevocably, liver failure and carcinoma. Hepatitis C virus (HCV), the causative agent of hepatitis C, is a blood-borne infection that is transmitted by shared needles, blood transfusion and childbirth. In Kingdom of Saudi Arabia, around 1.5% of the population is suffering from HCV, where the transmission rates are high among certain risk groups such as renal dialysis and haemophilia patients. Treatment of hepatitis C is still under careful development, and the three classes of medications currently available drugs act through the inhibition of the viral NS3/4A protease by binding to the substrate site of the enzyme. Conversely, both drugs are used for treatment of the HCV genotype-1 while most of Saudi patients are affected by HCV genotype-4. In this research proposal, focus on the design of non-peptide mimics of the viral protein NS4A that compete with this viral cofactor on its binding with NS3 protease, an important enzyme for the maturation of the virus. The aim of our presented work is to study the virtual screening of a large array of compounds belonging to the scaffolds 1,2,3,4-tetrahydro-1,7-naphthyridine (THNt). Automatic docking by Surflex-Dock™ furnished a top compound THNt-1 that appears promising in its docking because it has maintained several hydrogen bonds that are important for the binding of the core part of the NS4A. What is more striking is that the THNt-1, through its cycloheptyl group, made a hydrophobic binding attraction in a deep pocket composed of Val-33, Leu-44 and Val-107. This compound will be synthesised and will be tested and subjected for further target validation studies.Towards validation of novel Hepatitis C virus drug target via computer-aided molecular design.

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Introducing green chemistry into the undergraduate curriculum

Daniel J. Swartling1,2, [email protected]. (1) Tennessee Tech Univ, Cookeville, Tennessee, United States (2) Swartling Green & Sustainable Chemistry Group, Cookeville, Tennessee, United States

Our lab has recently developed a parabolic solar reflector to be used to heat chemical reactions (Agee, Brian M.; Mullins, Gene; Swartling, Daniel J. ACS Sustainable Chemistry & Engineering (2013), 1(12), 1580-1583). It has been used for several organic reactions, including the Diels-Alder reaction (Shikha Amin, Ashley Barnes, Courtney Buckner, Jordan Jones, Mattie Monroe, Leon Nurmomade, Taylor Pinto, Samuel Starkey, Brian M. Agee, David J. Crouse, and Daniel J. Swartling J. Chem. Educ., 2015, 92 (4), pp 767–770). To further expand the use of the parabolic reflector, this study looks at the dehydration of alcohols to form alkenes, a common reaction in the undergraduate organic laboratory experience. This combines solar thermal heating with distillation. This involves Green Principles #6 (design for energy efficiency) and #1 (prevent waste) . The overall reaction yields and general procedure will be discussed.


Effective approaches to integrating green chemistry in undergraduate organic chemistry courses

Sudhir B. Abhyankar, [email protected]. Chemistry and Environmental Science, Grenfell Campus, Memorial University of Newfoundland, Corner Brook, Newfoundland, Canada

Second and third year organic chemistry courses in most colleges and universities provide greater opportunities to teach the principles and practices of green chemistry in the lecture and laboratory. We have designed, developed and modified a number of experiments where students learn and apply the principles of green chemistry. Students use solid-state reaction conditions, microwave radiation, greener solvents and biomaterials to carry out stereoselective reactions. This presentation will focus upon different approaches to integrating green chemistry in undergraduate organic chemistry courses including independent student research projects in their fourth year


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Development of green problem-based learning experiments for the organic chemistry laboratory

Casey E. Wright1, Megan G. Kowalske2, James J. Kiddle1, [email protected]. (1) Western Michigan Univ, Kalamazoo, Michigan, United States (2) Chemistry & Science Education, Western Michigan University, Kalamazoo, Michigan, United States

Chemical educators have clearly shown the benefit to student learning by moving from the traditional expository format for laboratory experiments to problem-based experiments especially with regards to the development of critical thinking skills. In an effort to improve student learning outcomes as well as engaging the students through exposure to contemporary synthetic methods our research has recently focused on the evolution of our organic chemistry experiments to include the principles of green chemistry and problem-based experiences. In our presentation we will describe the efforts at our institution to improve the sustainability of our experiments and foster critical thinking skills through the use of problem –based learning experiences for our organic chemistry students.


Development of a green chemistry resource guide for the organic chemistry laboratory course in partnership with Sigma-Aldrich

Amy S. Cannon1, [email protected], Irvin J. Levy2,1, [email protected]. (1) Beyond Benign, Wilmington, Massachusetts, United States (2) Ken Olsen Science Center, Gordon College, Wenham, Massachusetts, United States

In the organic chemistry laboratory, green chemistry has been widely adopted as a means for reducing hazards and waste in the laboratory course, while maintaining the necessary rigor for teaching the subject. Through a partnership with Beyond Benign, a non-profit organization dedicated to green chemistry education, and Sigma-Aldrich, a resource guide has been developed for integrating green chemistry in the organic chemistry course. The resource guide features measurable benefits from implementing greener alternative organic chemistry labs, including waste reduction, economic benefits, and hazard reduction. The guide provides multiple pathways for adopting greener labs and points faculty members to options that can be tailored to suit the needs of their own department, and their own courses. The guide also provides an assessment of other benefits of green chemistry implementation, including energy efficiency, use of renewable resources, and use of safer solvents. The resource guide has been developed through a collaboration of Beyond Benign, Sigma-Aldrich, and a network of chemistry faculty from throughout North America.


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Learning green analytical chemistry using mobile phone local available materials in connection to culture

Wasin Wongwilai1,3, Kanokwan Kiwfo1,2, Nyesa Enakaya5, Kajorngai Thajee1,2, [email protected], Conrad H. Bergo4, Norio Teshima6, Tadao Sakai6, Kate Grudpan1,2. (1) Center of Excellence for Innovation in Analytical Science and Technology,Chiang Mai University, Chiang Mai, Thailand (2) Chemistry, Chiang Mai University, Chiang Mai, Thailand (3) Science and Technology Research Institute, Chiang Mai University, Chiang Mai, Thailand (4) East Stroudsburg University of PA, West Chester, Pennsylvania, United States (5) Chemistry, California State University, California, California, United States (6) Applied Chemistry, Aichi Institute of Technology, Toyota, Japan

Students can use local cotton cloth treated with indigo carmine or with simple extract of red maple leaf to learn green analytical chemistry. We found it possible to measure hydrogen peroxide fading of indigo. The rate law was found to be first order in dye and first order in hydrogen peroxide. Color changes of red maple leaf extract can determine acidity. Both methods use microliter scale quantities and a mobile phone camera as a detector. These methods enable students and the public to connect the culture of their traditional cotton cloth or local trees to green analytical chemistry. Traditional cloths of Thailand (Moh Hom), Japanese (Yukata) and US (blue jeans) will be discussed.


Green Contagion: How teaching green chemistry has inspired students to share green chemistry

Jane E. Wissinger, [email protected]. Chemistry, University of Minnesota, Plymouth, Minnesota, United States

Green chemistry has become one of the foundational elements of our sophomore level organic chemistry courses taught by ~45 teaching assistants (TAs) per year and taken by ~1100 students. The topic has captured the interest of a notable number of these TAs and students, especially those interested in academic careers at the high school and college level. The result been enthusiam for pursuing research opportunities by undergraduates in my group as well as enrollment in an upper division green chemistry lecture course. Also, collaborations with graduate students were established in developing new chemistries often related to their research. Examples will be given of contributions made by these individuals to new green curricular materials and how many have continued or plan to continue sharing the principles of green chemistry in their post-baccalaureate careers.


Teaching research: Designing molecular systems for greener advanced undergraduate laboratories

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Patrick Julien, pat[email protected], Jan Christopherson, Tomislav Friscic. Chemistry, McGill University, Montreal, Quebec, Canada

Effectively preparing advanced undergraduates for graduate research or industrial laboratories remains one of the largest challenges for undergraduate teaching laboratories. Green Chemistry is an important area of chemical research which enables chemistry previously considered incompatible with teaching laboratories to be integrated into the undergraduate chemistry curriculum. This work presents a system of experiments which integrates diverse Green Chemistry concepts and state-of-the-art asymmetric synthetic procedures in the teaching laboratory. In order to help students contextualize experiments, systems thinking is used to design a conceptual model of a topic, e.g. asymmetric catalysis, which is subsequently transformed into a flexible system of experiments which guides students through multiple approaches to catalysis, while introducing them to multi-step processes. By designing and tailoring reactions specifically to this model, we are able to develop procedures at the forefront of modern Green Chemistry research and introduce students to a wide range of concepts, instrumental methods, and practical techniques. The flexibility of these multi-step procedures enables the minimization of the traditional tradeoff between the scope and depth of material covered. This model of curriculum design allows instructors to easily adapt the curriculum to their needs, and gives students the ability to tailor it to their interests.


Integrating basic concepts of organic chemistry into the second semester introductory honors laboratory

Samuella B. Sigmann, [email protected]. Chemistry, Appalachian State University, Boone, North Carolina, United States

At Appalachian State University many of the students who enter the Honors College will pursue degrees requiring Introductory Chemistry. At Appalachian, the second semester laboratory section for the honors students has offered a platform where organic chemistry concepts can be introduced to this group of students. This is particularly relevant since many of these students, while not chemistry majors, will go on to take organic chemistry as required course work. In this paper, the modification of two experiments (Molecular Weight by Vapor and Freezing Point Depression) to include organic nomenclature and an introduction to functional groups will be discussed.


Starting with structure, bonding and spectroscopy: Introductory chemistry at Haverford College

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Robert C. Scarrow1, [email protected], Louise K. Charkoudian2, Karin S. Akerfeldt3. (1) Chemistry, Haverford Colllege, Haverford, Pennsylvania, United States (2) Chemistry, Haverford College, Haverford, Pennsylvania, United States

Six years ago, Haverford College launched a new two-year introductory sequence of Chemistry courses. The sequence starts with a course describing structure and bonding of both inorganic and organic compounds. This course is followed by semester courses on chemical dynamics (from a statistical mechanics approach), biological organic chemistry, and organic synthesis. In both the lecture and lab of the first semester course, students learn to use physical techniques (NMR, IR, GC-MS) to determine organic structure, and students also perform electronic structure calculations and visualizations available using WebMO to increase their understanding of the role of electronic structure in bonding. Thus, all students discover significant new chemistry in this course, regardless of whether they took AP Chemistry in high school. The advantages and challenges of our restructured curriculum will be discussed.


Integrating everything: Structure, reactivity and quantitation curriculum at CSB/SJU

Edward J. McIntee, [email protected], Annette F. Raigoza, [email protected], Chris P. Schaller, Kate J. Graham. Chemistry, College of Saint Benedict / Saint John's University, St. Joseph, Minnesota, United States

The Chemistry Department at the College of Saint Benedict / Saint John’s University has designed and implemented an innovative 4-year curriculum based on themes of structure, reactivity and quantitation. Traditional domains have been blended together to produce new introductory and foundation courses that serve chemistry, biochemistry and non-majors. These approaches have made a pronounced change in the first two years of our chemistry curriculum, including an introduction to structure, two semesters of reactivity, and a semester on quantitative aspects of chemistry. The goals of this approach include providing a better illustration of how chemistry is practiced in the twenty-first century as well as reinforcing basic concepts by demonstrating how they are applied across the fields of chemistry. Accompanying our curricular change, the department has moved to pedagogical approaches that reflect best practices from the literature. This presentation will provide performance and retention data as well as a perspective on the challenges involved in implementing a new curriculum.


Chemistry without adjectives: Teaching chemistry as a single, coherent science

John P. Bullock, [email protected], Janet B. Foley. Bennington College, Bennington, Vermont, United States

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Considerable attention has been focused on the efficacy of traditional chemistry curricula, yet in the past two or three decades the structure of the chemistry major at most institutions has changed only marginally. Ten years ago, we implemented a two-year sequence that integrates the major branches of chemistry, with intention of emphasizing their mutually reinforcing aspects. Our primary focus is on the chemistry of organic compounds, but we include many aspects of physical, inorganic, analytical and biochemistry to provide students with a more complete presentation that places the organic material in a broad and engaging context. Our goal is to clearly illustrate the practical and theoretical dimensions of chemistry as a working science, that is, as it is actually practiced, with little attention to the often arbitrary boundaries that separate its subdisciplines. This talk will describe our current curriculum model and what we see as its strengths as well as its challenges.


Organic chemistry-general chemistry-biochemistry: A pedagogic bridge circuit

Monica Ilies, [email protected]. Chemistry, Drexel University, Philadelphia, Pennsylvania, United States

Many students dread taking organic chemistry or biochemistry classes simply based on a priori judgments, which are usually rooted in bad experiences that other students had. "I hate organic chemistry!" sounds like the common fight-or-flight brain response when confronted with an inevitable threat. The core curriculum often imposes organic chemistry on these students. They end up struggling in such classes, which reinforces their initial bias. Actually, such students just become increasingly frustrated with not being able to connect the dots in the organic content. They feel there are always some missing links they will never find. Hence, memorization becomes their last resort. This presentation will describe an instructional method that uses basic knowledge of general chemistry (atomic structure, acid-base theory, polarity of bonds and molecules, VSEPR theory, intermolecular forces and other non-covalent attractive interactions, reaction coordinate, etc.) to introduce more difficult concepts in organic chemistry (C hybridization, bonding vs. antibonding molecular orbitals, nucleophiles vs. electrophiles, inductive vs. resonance effects, stereoselectivity, general steps of reaction mechanisms, etc.) and in biochemistry (basic notions of enzyme kinetics, introductory notions of drug design, etc.). This pedagogic technique targeted an Organic Chemistry III class. Students were juniors and seniors majoring in biological sciences, chemistry, health sciences, material sciences or biomedical engineering. Many of them were pre-med students. Students were constantly challenged to revise and use prior general chemistry knowledge to learn new organic content, solve problems and elaborate on daily life applications. Clicker questions and pop quizzes motivated students to keep the study pace constant throughout the term. The muddiest point technique was used for constant feedback. Overall, the integration of general chemistry with organic chemistry and basic notions of biochemistry had a positive impact on student performance and student evaluation.

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To get students to think like scientists – get them to read scientists

Janet B. Foley, [email protected], John P. Bullock. Bennington College, Bennington, Vermont, United States

We have been experimenting with various approaches to our chemistry curriculum over the past ten years. The challenge is to not only present ideas but have students understand and be able to apply those ideas to new situations. Right now our curriculum integrates general and organic chemistry from the first class. This allows us to present the “big ideas” of chemistry – solubility, structure, energy, etc – early on in our chemistry course sequence. One way we do this in class is to assign and discuss relevant articles from the literature that relate to topics in the curriculum. For example, in preparation for a discussion what kinds of questions can science can investigate, we have students read an article about the effects of estrogens on minnow populations in an experimental lake. Students write their critique of the study, interpret data presented in graphs, look at methods, and discuss their ideas with other students. We have found that this approach, not only captures the students’ interest, but also challenges them to connect ideas in a way that textbooks do not. I will present other examples of articles that we use and how we use them in our Chemistry 1-3 curriculum


Innovative technologies for chemistry instruction

Terence Laughlin, [email protected]. Chemistry, Blue Mountain School District, New Ringgold, Pennsylvania, United States

STEM, or science, technology, engineering and math, is an acronym that is commonly used when referring to fields of scientific innovation, education, economics and sustainability. It is used even more in referring to key areas of K-12 education. In a country where only 16 percent of high school seniors are proficient in mathematics, ranking the United States 25th in mathematics and 17th in science among industrialized nations, it is no surprise that STEM education has been elevated as a national priority. So just how do STEM educators go about tackling this problem? Are there innovative tools that can be integrated into classroom instruction that engage students and increase student understanding of science, technology, engineering and mathematics? More specifically, this presentation will address how a chemistry teacher can begin to integrate both technology and STEM concepts into their classroom.


Climate science in context; providing teachers with tools to elevate climate science literacy

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Gregory P. Foy1, [email protected], Leigh Foy2. (1) York College of Pennsylvania, York, Pennsylvania, United States (2) Science Department, York Suburban High School, York, Pennsylvania, United States

Inadequate climate science literacy in the United States is recognized by many as a leading issue in battling climate change. In a recent article “Climate confusion among U.S. teachers” in Science (Plutzer, et. al. 02/12/2016 p,664), the authors highlight a lack of understanding of the science as the main obstacle to effective teaching of climate science. While many teachers attempt to deliver climate science content in their classroom, their lack of knowledge and resources often results in delivery of misinformation. High school science teachers need to expand their climate science knowledge base and confidence in the subject matter and then need to find a seamless way to incorporate climate science in the traditional high school science curriculum. We are developing workshops that will help to build the climate science knowledge base for teachers, provide resources for classroom investigations, and provide climate science activities that will help to build contextual understanding of scientific concepts already taught in public schools. In this presentation, we provide a model of the workshop with the goal of providing a classroom ready activity that high school chemistry teachers can take back to their classroom and deliver with confidence.


ChemClubs — fun, food and outreach

Karen M. Kaleuati, [email protected]. American Chemical Society, Washington, District of Columbia, United States

The ACS ChemClub has a little bit of everything: education, fun, lab activities, outreach, grants, and more. Students who participate in the program are able to explore in chemistry through various activities and topics. The ACS ChemClub program is FREE to join and offers numerous opportunities, such as grants and contests, and resources—both online and in print—each year. Participants will be able to try out some fun food-based activities that are easy to incorporate into your classroom.


Why data collection?

Thomas M. Loschiavo, [email protected]. PASCO scientific, Roseville, California, United States

Collecting and analyzing the data has always been an integral part of chemistry labs. By moving beyond traditional experiments, the process of data collection and analysis can be used to address not only content standards, but also science and engineering practices. The analysis of collected data can also help facilitate the connection of the macroscopic, symbolic and sub-microscopic levels of representation. Finally, by putting

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data collection and analysis tools into the hands of students, we are opening up new avenues for student-led inquiry. Join me for this session to see how the process of data collection can foster science and engineering practices, connect levels of representation, and lead to meaningful student inquiry.


Creating a culture of safety in the science classroom

Regis Goode1, [email protected], Jennifer Bishoff2. (1) Ridge View High School, Columbia, South Carolina, United States (2) Southern Garrett High School, Mt. Lake Park, Maryland, United States

Generating general safety understandings for the laboratory setting is the responsibility of the teacher. It is imperative to create a culture of safety in the science classroom from day one. To be able to do that teachers need to understand the various aspects of safety. During this presentation the participants will examine important aspects of a safe science laboratory and will learn how to create a culture of safety in their science classroom. They will be provided with a pre-laboratory activity that they can adapt for their students to help create a culture of safety.


Edible material science/chemistry with kitchen chemistry

Sherri C. Rukes, [email protected]. Libertyville High School, Libertyville, Illinois, United States

Break the rules for once; allow food in the classroom! No need to struggle to interest your students when they get to eat these lessons. Using common ingredients that are found in the kitchen, learn how to teach concepts in materials science and chemistry with these activities. Concepts such as crystal formation, stoichiometry, solution chemistry, acid base chemistry, redox chemistry, mechanical properties as well as physical properties can be taught by simple everyday recipes that students will love to create. See how making fudge, cookies, candy glass and other foods can be used in the classroom. Discover a variety of hands-on science activities that you can do in the classroom tomorrow!


INOR: Synthesis and characterization of SNS pincer ligand precursors and zinc(II) complexes

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John R. Miecznikowski1, Tyler Ostrowski1, [email protected], Margaret Siu2, Kilee Bayne1, Nicholas A. Bernier3. (1) Fairfield University, Fairfield, Connecticut, United States (2) Department of Chemistry & Biochemistry, Fairfield University, Fairfield, Connecticut, United States

Recently, we have developed and synthesized a series of tridentate pincer ligands, each possessing two sulfur- and one nitrogen-donor functionalities (SNS), based on bis-imidazole or bis-triazole precursors. The tridentate SNS ligands incorporate thione-substituted imidazole or triazole functionalities. We have prepared somewhat rigid ligand systems through the use of 2,6-dibromopyridine as a ligand precursor. In addition, we have prepared more flexible ligand systems by employing the starting material 2,6-(dibromomethyl)pyridine to introduce a methylene linker into the pincer ligand. We have metallated these ligand precursors to form zinc(II) complexes containing these tridentate ligands. We are now interested in preparing ligand precursors based on 1,2,4 triazoles instead of 1,3,4 triazoles, which were previously prepared in the Miecznikowski Laboratory (Figure below). The goal is to metallate the novel ligand precursors with zinc(II) and copper(II) salts. A detailed description of the syntheses, and characterization (NMR Spectroscopy and ESI-Mass Spectrometry) of the SNS zinc(II) complexes and ligand precursors will be presented.

SNS Pincer Ligand Precursors based on 1,3,4 and 1,2,4 Triazoles


INOR: Synthesis and characterization of cobalt(II) model complexes for liver alcohol dehydrogenase

John R. Miecznikowski, Sheila Bonitatibus, [email protected]. Fairfield University, Fairfield, Connecticut, United States

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Recently, we have developed and synthesized a series of tridentate pincer ligands, each possessing two sulfur- and one nitrogen-donor functionalities (SNS), based on bis-imidazole or bis-triazole precursors. The tridentate SNS ligands incorporate thione-substituted imidazole or triazole functionalities. We have prepared somewhat rigid ligand systems through the use of 2,6-dibromopyridine as a ligand precursor. In addition, we have prepared more flexible ligand systems by employing the starting material 2,6-(dibromomethyl)pyridine to introduce a methylene linker into the pincer ligand. We have metallated these ligand precursors to form zinc(II) complexes containing these tridentate ligands. We are now interested in preparing cobalt(II) complexes that contain these ligand precursors. The cobalt(II) complexes will be cobalt model complexes for liver alcohol dehydrogenase. A detailed description of the syntheses, and characterization (NMR Spectroscopy and ESI-Mass Spectrometry) of the SNS cobalt(II) complexes and ligand precursors will be presented.


Understanding lanthanide-ligand interactions and the trans influence: A study using the CSD

Guilherme Borges2, [email protected], Shyam Vyas1, John Brennan3. (1) Center for Integrative Proteomics Research,, Cambridge Crystallographic Data Centre, Piscataway, New Jersey, United States (2) Rutgers University, Holmdel, New Jersey, United States (3) Chemistry and Chemical Biology, Rutgers University, Piscataway, New Jersey, United States

The trans influence is a widely understood phenomena that is frequently seen in the covalent metal-ligand interactions of transition metal complexes. Recent publications have indicated the presence of the trans effect in lanthanide complexes1, where the lanthanide-ligand bond length is influenced by properties of the ligand trans to the bond being analyzed. The Cambridge Structural Database (CSD)2,3 was used to identify and compare similar lanthanide-ligand interactions to determine how different ligand properties ultimately affect the interactions between the metal center and the donor atom of the ligand. A variety of different examples of the trans influence have been analyzed, proving that the effect is a fundamental property of lanthanides, much in the

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way it is for transition metals. The concept of matched molecular pairing was also implemented to further analyze how ligand properties influence the interactions between the donor atom of the ligand and the lanthanide center. It has been shown that inductive effects and chelation play a significant role in the lanthanide-ligand bond length.


Reactivity of Monosubstituted Palladium-Calixarene Complexes

Madison De Hoyos, [email protected], Bernat A. Martinez-Ortega. Department of Chemistry, Geosciences, and Physics, Tarleton State University, Stephenville, Texas, United States

Calixarenes are macrocyclic oligomers composed of four or more phenols bridged with methylene groups made by the reaction of para-phenol derivative and formaldehyde in basic conditions. Calixarene chemistry has been extensively studied due to its unique characteristics: complexing abilities, conformational flexibilities, structure and reactivity. The ability of calixarene to have different conformational flexibilities and the presence of hydroxyl groups makes an excellent ligand, capable of support more than one transition metal depending on the ring size. Metallo-calixarene chemistry is moderately studied and reported in literature. These metallo-calixarene complexes includes block s and p elements and some d elements (Ti, Cr, Mo, V, Nb, Ta, W, Mn, Re, Fe, Rh, Pt, Cu, Zn). However, few examples describing the selective addition of two metals has been reported. In our research group we were able to develop a synthetic method to selectively produce the first example of a monosubstituted palladium-calixarene complex. In our ongoing research goal we are trying to selectively add a second transition metal to the lower rim. We believe, that hetero or homo-bimetallic calixarene complexes can have potential as a novel multifunctional catalysts in which the two metals react in a cooperative manner. In this presentation we will discuss our findings over palladium containing-calixarene chemistry.


Synthesis and characterization of dioxo-molybdenum(VI) calix[5]arene complexes

Caleb Murphy, [email protected], Bernat A. Martinez-Ortega. Department of Chemistry, Geoscience, and Physics, Tarleton State University, Cleburne, Texas, United States

Calixarenes can be used as a poly oxo-surface support for active transition metals to produce a novel catalytic transition metal containing-calixarene complex (TMCx). The advantage of using such TMCx is that the resulting compound can be studied in solution either to obtain a full characterization of the complex or to follow the transformation of the substrate into a final product by 1H-NMR spectroscopy. Calixarenes are macrocyclic molecules composed of methylene-bridged phenol rings containing R groups on the upper rim and the hydroxy groups on the lower rim. It is these hydroxy groups that

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provide the necessary platform for the transition metal to be supported. Few transition metal containing calix[5]arene complexes have been reported in literature. Due to this finding, we are exploring the reactivity of the calixarene to selectively produce TMCx. In our early studies on transition metal containing calixarene chemistry, we found that the calixareme chemical reactivity could be affected by the type of transition metal to be used, pKa effect, calixarene conformation and the stability of the resulting TMCx. In this presentation we will discuss the discoveries of our recent studies of using dioxo-molybdenum(VI) moiety containing complex towards the reactivity of calix[5]arene ligand.


ANLY: GC-MS analysis of unprecedented whiskey flavors created by a novel aging process

Christopher Wright, [email protected], Regan Silvestri. Lorain County Community College, Elyria, Ohio, United States

Gas Chromatography-Mass Spectroscopy (GC-MS) can be readily utilized to generate an analytical profile of flavor compounds in whiskey. This method has successfully been applied to bourbon whiskies produced by a novel accelerated aging process which employs pressure, as opposed to conventional time, to mature the whiskey. New experimental flavors of whiskey have been generated which are completely original, having been made possible only by this innovative technology of accelerated pressure aging. These unprecedented bourbon whiskey flavors include cherry, apple, hickory, maple and honey locust. The distinct flavor compounds in these uniquely flavored bourbon whiskies have been identified and profiled using routine straight injection GC-MS. Accordingly, it has been observed that cherry bourbon, as compared to traditional oak flavored bourbon, has more ethyl octanoate, -a compound known to impart a sweet fruity flavor. Furthermore, it has also been observed that cherry bourbon has less phenethyl alcohol than traditional oak bourbon, -a compound known to impart a floral and bready flavor.


ANLY: Novel nucleophilic substitution-based turn-on fluorescent probes for hydrogen sulfide detection and biological application

Yuesong Hu1,2, [email protected], Liangwei Zhang1. (1) State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, China (2) Department of Chemistry & Biochemistry, Montana State University, Bozeman, Montana, United States

Since H2S plays a significant role in human health and disease, currently many methods such as colorimetry, gas chromatography, electrochemical analysis and fluorescent probes are used to monitor H2S in different conditions. Herein, we designed a novel

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naphthalimide-based turn-on fluorescent probe to detect H2S based on the azide reduction and nucleophilic reaction. As the sulfoxide group is a strong electron-withdrawing group, the naphthalimide was connected to it-followed by a chain linking the azide to quench the fluorescence. When this new compound touches H2S, the azide will first be reduced to the amine, then the N atom in the amine can attack the carbon next to the sulfoxide group and replace the position of the sulfoxide. As a result, the fluorescence is enhanced largely due to the electron-donating effect of the amine. To obtain this kind of compound, different kinds of reagents, including Cys, aminothiophenol, aminoethanethiol, etc, were used to react with naphalimide. The electron sensitive group in the top of the naphalimide was also changed to improve sensitivity of NH-nucleophilic substitution reaction. These probes were highly sensitive towards H2S and could be used to image H2S in living cells.



Assessing general chemistry students' ability to translate between multiple representations

Xiting Lin, [email protected], Ji Son, James A. Rudd. California State University, Los Angeles, Los Angeles, California, United States

Translating between scientific representations is crucial to demonstrating expert understanding of science concepts; however, such translations are difficult for science novices (e.g., students). In chemistry, for example, students can balance chemical equations without understanding the molecules or reactions that they represent. In the chemistry triplet model of chemistry education, translations can occur between macroscale, nanoscale, and symbolic representations. Previous studies have shown that translating between the three representations in the chemistry triplet increases expert-like thinking. In our research, we investigated asymmetries in students’ ability to translate between representations in the chemistry triplet. In one study, undergraduate students enrolled in a general chemistry course were asked translation questions in a 3x2, representation (macroscale, nanoscale, and symbolic) x direction (e.g., nano-to-macro vs. macro-to-nano), ANOVA within-subjects design. Students struggled with

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translations involving nanoscale representations (e.g., circles representing atoms) relative to those involving symbols (e.g., equations) and macroscale phenomena (e.g., reactions and substances at the human scale). In a subsequent study, we investigated chemistry students’ understanding of the nanoscale by asking them to interpret nanoscale phenomena described with words and represented with pictures. Undergraduate students enrolled in a first general chemistry course were asked translation questions in a 2x2x2, representation x direction x modality (word vs. picture), ANOVA within-subjects design. Students performed significantly better when the nanoscale was described in words than when depicted with pictures. Developing and studying approaches to teaching and assessing chemistry understanding of the atoms and molecules in the nanoscale may be essential for promoting a meaningful understanding of chemistry.


Bonding with Bithlo: Enhancing the Quality of K-12 Science Education in an Underprivileged Community

Lauren Gandy3,4, [email protected], Yuen Yee Li Sip1, Bailey L. Mourant1, Stephen M. Kuebler2. (1) Burnett School of Biomedical Sciences, University of Central Florida, Orlando, Florida, United States (2) Chemistry Dept, University of Central Florida, Orlando, Florida, United States (3) Chemistry - Forensic Science, University of Central Florida, Orlando, Florida, United States (4) Analytical Chemistry, National Center for Forensic Science, Orlando, Florida, United States

Bithlo, Florida is an unincorporated community of roughly 8,500 people on the outskirts of Orlando. Earning less than half of the national average income, an estimated 16.1% of Bithlo residents live in poverty, 11% are unemployed, and only 23.1% of the community is college educated. Bonding with Bithlo is a new program funded by the ACS New Activities Grant through which the ACS Student Chapter at the University of Central Florida (ACS@UCF) hosts hands-on science classes at Orange County Academy (OCA) in Bithlo, Florida. The primary goal of this project is to teach students about the fundamental importance of the STEM fields through engaging experiments and real-world applications, as well as the value of pursuing a higher education. OCA science classes are often taught en masse to middle school and high school level students simultaneously. ACS@UCF has created interactive experiments individualized to grade level that illustrate and reinforce scientific principles for students ranging from 3rd grade through 12th grade. Our talk explains the creation of the project and subsequent execution of outreach visits, including the successes and difficulties that arose throughout our journey.

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Bonding with Bithlo students celebrating a successful visit with the ACS@UCF volunteers.


In silico experimentation across green chemistry

Subhasish Chatterjee, [email protected]. Chemistry MMA .MR1024, The City College of New York, CUNY, New York, New York, United States

Renewable resources and novel design approaches are key factors for implementing fundamental green chemistry principles in a classroom setting. Computer simulations provide an attractive approach to weigh up a broad range of chemical science research with real-world applications. Open-source software and potent personal computing devices also open up convenient avenues for new research paradigms and learning opportunities. Notably, hands-on examples involve basic computer simulation methodologies such as Monte Carlo, Brownian dynamics, and Molecular dynamics in predicting the physicochemical properties of environmentally important and biologically relevant systems. This current work illustrates the structural organization of renewable amphipathic biomaterials, as well as DNA-based nanomaterials for biochemical sensing and biomedical applications.


Investigation of putative bacterial laccases in a biochemistry laboratory course

Robert E. Collins, [email protected]. Physical Sciences, Eastern Connecticut State University, Hamden, Connecticut, United States

This year, I piloted a laboratory module in the Biochemistry II laboratory course at Eastern Connecticut State University, a small, public liberal arts university. This project includes structural and sequence analysis, design of expression constructs, protein expression and enzymatic characterization. Laccases (EC are multi-copper

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oxidases with diverse substrates. High-redox fungal laccases are capable of depolymerizing lignin and cleaving rings of aromatic compounds. Laccases are sought after in biotechnological applications including biofuel production, enzymatic wastewater treatment, pulp bleaching for paper, and enzymatic biofuel cells. Despite the range of potential applications, there are few laccases that are expressed at high levels in E. coli, thwarting facile production of laccases. Recombinant expression is essential for design or directed evolution of laccases tailored to specific applications. Until recently, it was thought laccases were limited to eukaryotes (plants, fungi and insects), but there have been reports of bacterial laccases with modest redox potential. Bacterial enzymes, which lack the complex glycosylation of fungal enzymes and fold without the complex chaperones of the eukaryotic secretory pathway, should be more amenable to recombinant expression in E. coli. To explore this possibility, students searched bacterial and archaeal genomes for homologs of fungal laccases. They identified proteins with 25-30% identity to fungal search sequences. Using sequence motifs they had identified in fungal sequences and had confirmed in laccase crystal structures, the students confirmed all copper binding sites were present. From a list of candidate laccases, three genes were prioritized based on bacterial properties: thermophilic, halotolerant, and a bacteria that antagonizes the growth of a laccase producing fungus. The three candidate laccases are from different phyla (Actinobacteria, Proteobacteria, Firmicutes). The students designed and ordered constructs for expression of tagged proteins. They transformed the expression vectors into E. coli, and then expressed, purified and characterized putative bacterial laccases. In keeping with the theme “Chemistry of the People, by the People, for the People” I will reflect on the engagement of students in a project with potential industrial applications and consider how to best expand such efforts in a small liberal arts setting.


Instructional laboratory chemical waste minimization through miniscale experiments: Development of a planning and implementation model for University of San Agustin Chemistry Department using lessons learned from New Jersey City University

Aylen Badilla Wargniez1, [email protected], Robert G. Aslanian1, Aileen V. Vergara2, Aneline P. Tolones2. (1) Chemistry Department, New Jersey City University, Jersey City, New Jersey, United States (2) Chemistry Department, University of San Agustin, Iloilo City, Philippines

Use of miniscale experiments in the first two years of teaching chemistry laboratory courses has been gaining popularity in the United States in response to the stringent federal and state safety and environmental regulations. However, in the Philippines, where safety policies and chemical waste treatment infrastructure are lacking, use of miniscale experiments in instructional chemical laboratories can be a practical and sustainable solution. This presentation highlights the development of a planning and implementation model of miniscale experiments for the Chemistry Department in

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University of San Agustin located in central Philippines, using New Jersey City University’s experiences and lessons learned from teaching the miniscale experiments for over ten years. This presentation also emphasizes the importance of international collaboration in addressing the needs and gaps in delivering improved chemical education programs in developing countries.


Teaching green chemistry and 3Rs: Resources, responsibility, and recycling

Ann E. Shinnar, [email protected]. Chemistry Dept, Lander College for Men/Touro College, Kew Gardens Hills, New York, United States

In order to familiarize college students with principles of green chemistry, we have introduced an annual lecture and laboratory session into our general chemistry curriculum. Our lecture is scheduled in the spring semester close to Earth Day and focuses on 3Rs. Since 1970, the 3Rs have referred to “reduce, reuse, and recycle.” For instructional purposes, however, we have implemented a variation of the 3Rs: resources, responsibility, and recycling. Key lecture topics focus on materials widely used in our daily lives: aluminum, glass, plastic polymers, and batteries. Lecture content also reviews classic chemical principles such as redox chemistry in Hall-Heroult process for manufacturing aluminum and physical properties of glasses composed mainly of SiO2. Coverage of polymers includes an overview of step-growth versus chain-growth polymers, plastic recycling symbols 1-7 established by the Society of the Plastics Industry Inc. (SPI), and identification of different plastic resins via their signature IR spectra. Following lecture, students enter the chemistry lab where they categorize >30 household items including a variety of plastic food containers, reusable plastic bags, metal cans, and batteries. We also test packing peanuts of Styrofoam versus starch by contrasting their solubility with acetone versus water. The combined lecture and laboratory sessions provide an opportunity to incorporate principles of green chemistry in a manner that complements our standard college science curriculum. Students show overall enthusiasm for our 3Rs integrated experience.


Development and implementation of greener chemistry laboratory modules with a focus on current academic and industrial research

John de la Parra, [email protected], Thomas R. Gilbert, Vaso Lykourinou. Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts, United States

We have undertaken the redevelopment of our undergraduate laboratory courses to focus on two major themes: greener methodologies and a tie to ongoing, real world research. In the modern research environment, these are vitally important pedagogical goals for training a future generation of responsible scientists. This work represents the

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first semester of modules aimed at engaging the college freshman chemistry student. Each module consists of 4 laboratory sessions and culminates in group presentations, sharing of data, and discussion. In our pilot module we focused on the creation of biofuels from algae. This project represented an ideal synthesis of the principles of green chemistry as well as incorporating current research on our campus. We then moved to the development of an extraction and analysis of pharmaceutical compounds from a medicinal plant using greener methodologies. Again, this tied directly to research being conducted by our faculty. Additionally, with the help of student-led teams, we have developed a module that uses the green catalyst, Fe-TAML, to demonstrate the dynamics of reaction kinetics. Lastly, we will present work on a novel atomic absorption module that demonstrates fundamental chemical principles while also incorporating forensic lab testing procedures.


Green chemistry and sustainability at the high school level

Zachary T. Lachance2, [email protected], Hamish S. Christie1, Jeanne E. Pemberton2. (1) Univ of Arizona, Tucson, Arizona, United States (2) Dept of Chemistry, University of Arizona, Tucson, Arizona, United States

The ideas of “Green” chemistry and sustainability are important to all areas of chemistry and introducing these ideas at the earliest levels of chemistry education should be an important goal. To this end, a summer course about green chemistry and sustainability is being developed for in-service high school chemistry teachers. The course will provide teachers with an understanding and knowledge of green chemistry and sustainability and also with materials (modules and experiments) that can be used in high school classrooms. This course, and the affiliated modules, will communicate central chemical ideas and principles using interesting and relevant examples of green and sustainable chemistry. At the center of this project are the “modules”. These have been developed as vehicles to teach chemical concepts, by investigating the fundamentals of chemistry that are important in green chemistry ideas and examples. Each module is accompanied with a “teacher’s guide” that provides useful information about how the module might be integrated into an existing curriculum. All modules are also supported with an “activities/experiment” document, which contains a relevant lab experiment and other in-class activities, and a “supplemental information” document that provides additional information and also more detail about potentially difficult topics. The series of modules have been developed with a level of flexibility that allows them to be used either individually or as a connected group.


Sustainable design science café

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Randy A. Weintraub1,3, [email protected], Barbara Ameer2. (1) Science, Math and Technology, Rowan College at Burlington County, Pemberton, New Jersey, United States (2) Medicine, Rutgers Robert Wood Johnson Medical School, Princeton Jct, New Jersey, United States (3) Residue, Metabolism & Environmental Fate, JRF America, Audubon, Pennsylvania, United States

One of goals of ACS Princeton Local Section is excellence in education outreach. Drawing together the knowledge and experience of individuals from three different sectors of society, we created a Science Café to communicate principles and actions of environmental sustainability. A prominent university’s director of design and construction, a federal government agency’s project leader research engineer, and a principal at a leading global architectural design firm, all focused their presentations on the importance and advances in sustainable design. Teachers, students, general public and area ACS local section members took part in this event that raised awareness and concern about the stewardship of environmental sustainability. The brief presentations: Frick Chemistry Laboratory—Still Green After Five Years, Permeable Pavement, and Sustainability Works at the Princeton Library and Beyond, inspired younger attendees to consider career directions in sustainability in general and, material science, environmental chemistry and recycling natural resources, specifically. This outreach activity was complementary to Princeton University’s leadership among academic institutions in the country in sustainable design, sustainability research projects at regulatory agencies, and socially responsible sustainability design approaches in the private sector, to include greater communication with the populus in the local region. The nearly 75 participants were able to reflect upon their attitudes and judgments with regard how they contribute to ensure long-term environmental sustainability. They are likely to think more deeply about environmental sustainability as they make choices in purchases and living styles, and vote on public policy referendums issues and elect candidates to office.


Linking concepts to actions in the context of the general chemistry laboratory

George R. Long, [email protected], Marcus Hewitt. Chemistry Department, Indiana Univ. of PA, Indiana, Pennsylvania, United States

The General Chemistry laboratory plays an integral role in the education of most students in STEM or STEM related majors. Ultimately, the overarching goal of the laboratory is for students to learn to use conceptual knowledge to inform their actions in the real world. The laboratory provides an important behavioral environment, where a series of psychomotor tasks provide a context for the concepts used to predict or explain the observed results. In fact, the specific learning environment will instantiate the target concept and serve as a part of the learner’s schema. Social context and

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rationale is provided through a specific capstone activity. Some examples of our capstone activities include mass and volume measurements, and solution making applied to medical IV fluids, density measurements are applied to efficacy of radiator fluids and titration is applied to analysis of food products, and environmental samples. This study focuses on student perceptions and mental models developed in the laboratory context, their link to the psychomotor activities, and students ability to successfully complete the capstone activity. We are interested in the connection between the specific psychomotor activities used to teach specific chemical concepts, and the learner’s ability to apply those concepts in a wider social context.


Exploring the relevance of chemical identity in biochemistry contexts

Courtney Ngai, [email protected], Hannah Sevian. Chemistry Department, University of Massachusetts Boston, Boston, Massachusetts, United States

Biochemistry has been long recognized as an interdisciplinary field, and often draws on chemistry concepts to help explain biochemical phenomena. Various policy documents (e.g. A New Biology for the 21st Century, NRC, 2009) have called for reform in undergraduate biology and biochemistry education, which can include reinforcing general chemistry concepts that are relevant in biochemistry. Chemical identity is one such general concept in chemistry, and involves identification and differentiation of substances (Sevian & Talanquer, 2014). Since chemical identity is a foundational concept in chemistry, we hypothesize that chemical identity thinking is also relevant for understanding and applying biochemistry concepts, and potentially critical to development of expertise in biochemistry. This study first surveyed experts in biochemistry to identify biochemistry contexts where chemical identity concepts are considered relevant. The survey asked participants to describe their own work, whether they thought chemical identity thinking was relevant to their work, and to provide an example of a problem in which they consider chemical identity thinking to be relevant. These responses were analyzed to find the types of biochemistry problems that repeatedly emerged as relevant to chemical identity thinking, and then used to design contexts for use in creative exercises. Creative exercises are an open-ended assessment tool that has been used in chemistry (Ye & Lewis, 2014) and biochemistry courses (Warfa & Odowa, 2015) to analyze the linkages between foundational chemistry concepts and upper-level courses. The creative exercises developed in this study were implemented in an undergraduate biochemistry class (N=30) to determine what chemical identity concepts students considered to be relevant. Analysis of these data revealed the linkages students made between biochemistry contexts and chemical identity thinking, and were compared to the links made by the surveyed disciplinary experts.


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Chemistry teachers' learning in context of scientific texts via conceptual modelling

Rea Lavi1, Dov Dori3,2, Yehudit Dori1, [email protected]. (1) Faculty of Education in Science & Technology, Technion, Haifa, Israel (2) MIT, Cambridge, Massachusetts, United States (3) Faculty of Industrial Engineering & Management, Technion, Haifa, Israel

Learning in context of scientific texts poses a challenge to many chemistry teachers. To cope with this task, we exposed about 30 pre- and in-service chemistry teachers taking part in a graduate chemical education course which applies Object-Process Methodology (OPM) for conceptual modelling. While concept maps allow for visual organisation of knowledge, OPM offers extended capabilities, as it combines graphical and textual representations, using a compact set of modelling elements. The research objective was to examine the effect of conceptual modelling on teachers' understanding of two adapted, context-based scientific texts. One text related to gecko’s surface sticking ability and the other to proliferation of cyanobacteria. Teachers read the text in two class sessions, one month apart from each other. Working in teams, the teachers' task was to identify key concepts and use them to construct an OPM model. The figure below shows an example of a model of the gecko phenomenon and its possible application that one team created. Teachers reported that using OPM for conceptual modelling improved their understanding of the scientific text and fostered their systems thinking by better organizing their knowledge. We found that OPM can serve as a vehicle for expressing and communicating key concepts, their context, and relations among them. We discuss our findings and implications for chemical education.

A conceptual model of the gecko phenomenon


Good practical science

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John Holman1,2, [email protected]. (1) Department of Chemistry, York University, York, United Kingdom (2) President Elect, Royal Society of Chemistry, London, United Kingdom

Experimentation is a vital context for science. For most teachers, science without experiments would be like teaching literature without books. Yet practical, laboratory-based learning is under pressure in systems which emphasise testing and examination, and from limitations of time and funding. In this presentation I will describe an international comparative project that I am carrying out for the UK’s Gatsby Foundation, looking at practical lab work in school science in six countries: the Netherlands, USA (Massachusetts), Singapore, Australia (Victoria), Finland and Germany. How does practical science take place in countries of the world with the highest performance in science? I will describe the emerging messages that signpost good lab-based science teaching by international standards, with particular emphasis on chemistry. Although the study is not complete at the time of writing this abstract, I am already struck by the deep conviction of the teachers that we meet of the importance of practical laboratory science. Their conviction helps to reinforce the conjecture that, as the virtual world becomes more accessible and realistic, authentic experience in the real world becomes more, rather than less, important for learning.


Inquiry-based learning in authentic outdoor contexts

Tali Tal, [email protected]. Education in Science and Technology, Technion, Kfar Vradim, Israel

Inquiry-based learning is advocated in all scientific disciplines. It is viewed as student-centered, thought-provoking method to engage students in doing science and in learning how science is being done. Nonetheless, inquiry learning faces many challenges which are the result of ambiguity regarding inquiry learning, limited understanding by teachers, over emphasis on procedures and on the hands-on rather than on the minds-on components and insufficient time for meaningful learning in an era of international testing and commitment to accountability. To address the challenge of insufficient understanding of what inquiry learning is, and to broaden the teachers' views of the multiple ways inquiry learning can take place, we offered in-service teachers a real-context outdoor inquiry-based learning experience. It consisted of three investigations in different contexts, fields and genres: an ecological, sociological and archeological ones focusing on the natural world, the social and the material ones. We expected that teachers will develop more complex view of inquiry learning that will include epistemic aspects and deeper understanding of inquiry as a generative method for knowledge construction and for metacognitive thinking. Following the teachers work

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in the website we designed where they posted artifacts and reflections and through interviews and observations, we found substantial change in their views of inquiry-based learning. They identified similarities in the three fields in asking meaningful questions, seeking ways to address them, collecting and analyzing data and communicating results. They all addressed the authentic contexts of the investigations and recognized the contribution of the real context to their own learning and to their students' learning after they apply what they learned. As science teachers, many acknowledged, for the first time, that archeological and sociological research is "scientific" too. They pointed to the outdoor environment as engaging and motivating to learn and to the affective outcomes this environment provides to learners.


Museum Smell Bar experiences connect chemistry to the familiar and to the relevant in visitors’ lives

MJ Morse, [email protected]. Current Science & Technology, Museum of Science, Boston, Massachusetts, United States

In a museum, without offering the reward of grades or degrees, exhibits and other learning experiences compete for the extremely limited time and attention of visitors with the aspiration of inspiring an individual’s intrinsic motivation, rather than transferring knowledge per se. Visitors arrive with varying backgrounds and education, with varying levels of familiarity with the English language, with varying physical and cognitive abilities. And unlike a classroom, a museum setting is a physically active, noisy environment with people coming and going at will. Our initial premise was that the prospect of smell might attract visitors. The chemistry itself was constrained by the necessity that any chemicals we used not require a hood, or be extremely long-lived or be irritating or allergenic. Odorant chemicals needed to be distinctive, detectibly different from one another and illustrate specific molecular properties. We designed each Smell Bar with three components: an entry point or ‘cognitive ramp,’ a chemistry experience, and a direct connection to visitors’ lives. Furthermore, we required that the concept had a current research component. The chemistry experiences were bookended by the familiar, the relevant, and the cutting edge research. The choice of smell as a vehicle proved to be fortuitous and visitors appear to be irresistibly drawn to smells and the activity of smelling. Smell served as a powerful hook in talking about chemistry. Surveys and evaluation interviews indicated some success in chemistry understanding.


Developing higher-order thinking skills through reading web-based texts in the context of green chemistry

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Yael Shwartz1, [email protected], Eldad Marom1, Yehudit Dori2. (1) Sicence teaching, Weizmann Institute of Science, Rehovot, Israel (2) Science & Technology teaching, Technion – Israel Institute of Technology, Haifa, Israel

Traditional chemistry teaching focuses on teaching conceptual knowledge and key concepts to explicate standard problems, while context is viewed as secondary or supplementary to the concepts (Tytler 2007). Research reveals that students are able to solve problems using concepts learned, but merely in situations in which they were taught. This indicates low-level transfer ability of students' learning (Gilbert, 2006). Context-based curriculum is recommended as a mean to address the above mentioned challenges. Our study focuses on one of the three main questions leading this symposium - How is context-based learning useful to students in helping them develop cognitive skills necessary for using particular knowledge, when meeting a new context? The intervention consists on five web-based texts followed by tasks, in the context of green chemistry. These texts served as a framework for fostering the development of selected higher-order thinking skills- comparing and argumentation among 11th grade chemistry students. Each skill was assessed by in two levels of complexity: basic and advanced, and in two domains: scientific (chemistry) and socio-scientific. The context of green chemistry intrinsically evokes the use of these thinking skills and domains. For example the skill of comparing is required in order to compare green processes in respect to earlier (not quite “green”) conventional chemical practice. Green Chemistry was also found as a suitable context for application of knowledge that was already taught in class in a traditional manner. Assessment items, embedded in the web-based texts, involve syllabus related tasks as well as thinking skills tasks and were analyzed qualitatively and quantitatively. Finding indicates significant improvement in the following categories: basic comparing, socio-scientific argumentation and scientific argumentation skills. We also examined transfer of knowledge and skill in a manner that will be presented in the symposium.


Semester-long authentic research experience in snow chemistry in the general chemistry laboratory

Nathaniel May3, [email protected], Stephen McNamara3, Siyuan Wang3, Julianne Vernon2, John P. Wolfe4, Deborah Goldberg2, Kerri A. Pratt1,5. (2) Department of Ecology and Evolutionary Biology, University of Michigan, Ann Arbor, Michigan, United States (3) Department of Chemistry, University of Michigan, Ann Arbor, Michigan, United States (5) Department of Earth and Environmental Sciences, University of Michigan, Ann Arbor, Michigan, United States

A novel general chemistry laboratory course was developed to create an authentic research experience incorporating snow chemistry through the entire course. During the pilot offering in Fall 2015, students practiced general chemistry concepts through laboratory experiments in the context of snow chemistry. This course aimed to increase

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student interest and engagement by connecting laboratory experiments to real world problems such as the effects of road salt application on snowpack composition. In addition to traditional experiments, the students individually performed ion chromatography analysis of snow samples collected across multiple locations in the Alaskan Arctic to explore original research questions. The students individually presented their results through a public poster session and in a research manuscript. This course represents a demonstration of successful integration of active research into an entry-level course. Since STEM retention is a goal of this new research-based course, survey-based evaluation of the course will be discussed.


NSF programs in the Division of Undergraduate Education

Thomas B. Higgins, [email protected], Dawn Rickey. Division of Undergraduate Education, National Science Foundation , Arlington, Virginia, United States

The National Science Foundation (NSF) has several programs that support undergraduate education. This poster will highlight the four major programs in the Division of Undergraduate Education (DUE). DUE program officers will be on hand to answer questions. The four DUE programs are Advanced Technological Education (ATE), a workforce education program that helps students develop skills and earn credentials to get jobs in their communities; Scholarships in STEM (S-STEM), a scholarship program for academically talented and financially needy students earning STEM degrees; Improving Undergraduate STEM Education (IUSE), a program that improves student learning and prepares the scientific leaders of tomorrow; and Robert Noyce Teacher Scholarships (Noyce), a scholarship program for STEM majors who want to become K12 teachers.


Naming new elements

Paul J. Karol2, [email protected], Graham F. Peaslee1, [email protected], Robert A. Yokley3, [email protected]. (1) Department of Chemistry, Hope College, Holland, Michigan, United States (2) Chemistry, Carnegie Mellon University, Palo Alto, California, United States (3) Analytical Chemistry Consulting Service, Belews Creek, North Carolina, United States

How are new elements named? The International Union of Pure and Applied Chemistry (IUPAC) is responsible for soliciting and approving discoverers’ proposals for new names. Historically, elements have been named after geographical places, scientists, or source minerals, etc. Elements 114 (Flerovium) and 116 (Livermorium) were added in 2011 and were named after the laboratories which discovered them (Flerov Laboratory in Russia and Lawrence Livermore National Laboratory in the U.S.A).

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Discovery claims of elements 113, 115, 117 and 118, completing the 7th row of the Periodic Table, were recently accepted. A Russian-American team from Dubna and Livermore (as well as the Oak Ridge National Laboratory in Tennessee) will name elements 115, 117 and 118. Element 113’s discovery is by the Japan’s RIKEN laboratory. The process and history for naming new elements will be described together with the duties and responsibilities of the ACS Committee on Nomenclature, Terminology, and Symbols (NTS).


Working together to enhance diversity in the chemical sciences: The alliance for diversity in science and engineering cultivates the UC Graduate Consortium for Cultural Diversity in Chemistry to maximize inclusion and outreach in Cincinnati

DeVonna M. Gatlin3, [email protected], Crystal Valdez2, Steven A. Lopez1. (1) Chemistry & Chemical Biology, Harvard University , Cambridge, Massachusetts, United States (2) Chemistry , Stanford University , Stanford, California, United States (3) Chemistry , University of Cincinnati , Cincinnati, California, United States

The lack of diversity in STEM fields is a long-standing problem the scientific community faces. Despite the efforts of many organizations, including the National Science Foundation (NSF) and the National Institutes of Health, STEM fields still suffer from a lack of inclusivity. Many universities have acted upon these disconcerting trends and launched initiatives within their departments. In 2015, ADSE President Steven Lopez and Vice-President Crystal Valdez completed their Ph.D. degrees and formed the non-profit organization called The Alliance for Diversity in Science and Engineering (ADSE). The ADSE board supports, organizes, and oversees local, graduate student-run organizations that reach out to students and scientists of all ages and backgrounds. We connect scientists across the nation, showcase nontraditional career paths and underrepresented minority experiences in STEM, and educate students about opportunities in the sciences. The University of Cincinnati chapter is an outstanding example of our national network of graduate-student led chapters. UC Graduate Consortium for Cultural Diversity in Chemistry (CCDC) was co-founded by DeVonna M. Gatlin. The board of CCDC implement ADSE’s mission for diversity and inclusion and focuses on graduate student professional development. CCDC programing encourages graduate students to become role models for younger scientists, especially those unaware of the benefits of a graduate degree in STEM. To date CCDC has introduced The Diversity Lecture Series, hosting guest speakers Dr. Miguel A. Garcia-Garibay (UCLA) and Dr. Joseph S. Francisco (U. of Nebraska-Lincoln). CCDC has also partnered with the black youth mentoring group ‘Hearts and

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Minds’. These outreach events provide hands-on chemistry demonstrations for elementary schools in the Cincinnati area. CCDC is also developing a high school STEM scholar’s academy and professional development forums for their members. They seek to establish merit-based travel awards to help graduate students attend ACS national meetings.


Ethics in chemical research: An interactive discussion about questions, conflicts, and training

Patricia A. Mabrouk2,3, [email protected], Steven L. Tait1,3, [email protected]. (1) Indiana University, Bloomington, Indiana, United States (2) 115RI, Northeastern University, Boston, Massachusetts, United States (3) ACS Committee on Ethics, Washington, District of Columbia, United States

Ethical decision making is essential at all stages of the chemical research enterprise from project inception to lab work to reporting to production. This presentation seeks to stimulate discussion and consideration of ethical dilemmas and ethical training needs across the membership of the Society. At this interactive presentation, the ACS Committee on Ethics will engage attendees in discussion about ethical questions and concerns that they encounter in their work as well as needs and opportunities to strengthen ethical awareness, education, programming, and communication. We will also update attendees on new and emergent ACS activities and programming related to ethics in chemistry.


Undergraduate research: a case study of one lab at Meredith College

Alexandra B. Ormond, [email protected]. Chemistry, Physics and Geoscience, Meredith College, Holly Springs, North Carolina, United States

Meredith College (MC) is a primarily undergraduate institution, however, our undergraduate students actively participate in research, and our B.S. in chemistry degree requires one semester of research. During the semester, students take research courses for credit towards their major and for a grade. It is often easier for students to complete research over the summer, and through our Undergraduate Research Program, students can be funded for an eight-week summer project. Summer research projects at MC have had our undergraduates working with high school students in a mentorship environment. Students have also completed their honors thesis projects and worked on intensive literature reviews. When students take research for a grade, two tiers of research are available: Introduction to Research and Research. Introduction to Research often yields projects on literature reviews of topics of interest and is available for students who have not completed organic chemistry. The Research course is for students who have completed organic chemistry or have had some prior research

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experience and focuses on wet chemistry work. This presentation will discuss the different research projects held in one laboratory at MC since 2014 and their outcomes.


Using edible experiments to teach chemical principals

Patricia D. Christie1, [email protected], Markrete Krikorian2. (1) Experimental Study Group, MIT, Cambridge, Massachusetts, United States (2) MIT, Dept. of Chem., Cambridge, Massachusetts, United States

Students are much more likely to engage in a topic if they see relevance to their own lives. At the Experimental Study Group (ESG) at Massachusetts Institute of Technology (MIT), we encourage learning through hands on, interactive, small group learning. We usually are teaching the science General Institute Requirements (GIR) to undergraduates (mostly freshmen), but there is the opportunity to explore applications through seminars that anyone at MIT can take. We have been able to apply Chemistry to the topic of Sports (Chemistry of Sports, ES.010) and Kitchen Science (Kitchen Chemistry, ES.011) over the last 16 years. This talk will talk about the design, implementation and improvement of these seminars with emphasis on the Kitchen chemistry that was started in 2000. The kitchen chemistry course was redesigned this past Spring 2016 when Markrete Krikorian, a fifth year graduate student in chemistry wanted to help teach the course. Generally these edible experiments are designed to be completely within a 2-hour meeting. There is an experiment (recipe) done by the students, academic readings through the course textbook and research papers, and homework for each of the weekly meetings. There is also an opportunity for the student to peer teach an experiment to their friends near the end of the term. A short research paper on a topic of their choosing is also required to pass the seminar course. This has been a very successful seminar on campus with waiting lists every term it is offered. Markrete also organized a symposium open to the entire MIT community on selected topics including Thermodynamics of Searing, Coffee preparation, Ice cream and production of Beer through fermentation


Introducing planetary boundaries to chemistry curriculum

Alexey Leontyev1, [email protected], Renee P. Beeton1, Natalia P. Tarasova2. (1) Adams State University, Alamosa, Colorado, United States (2) Mendeleyev University of Chemical Technology, Moscow, Russian Federation

Planetary boundaries, a concept recently introduced by Johan Rockström and colleagues, define the safe operating space for humanity with respect to the Earth and are associated with the planet’s systems and processes. Being aware of planetary boundaries and the danger of crossing thresholds brings relevance to chemistry concepts and promotes responsible stewardship of the Earth. We developed a lesson to

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introduce the idea of planetary boundaries and the underlying chemistry concepts to students in a general chemistry class. The lesson integrates strategies that facilitate conceptual change and cooperative learning. We chose concept mapping to facilitate learning about planetary boundaries and help students see interconnections between chemistry concepts and different planetary boundaries, as well as interactions of planetary boundaries. We used several methods to assess cognitive, affective, and behavioral outcomes. Full details will be presented at the meeting.


Burg Teaching Fellowship at USC: An opportunity for graduate students to co-teach a class under the mentorship of the course instructor

Piyush Deokar, [email protected]. Chemistry 1661, University of Southern California, Los Angeles, California, United States

One major responsibility as a chemistry graduate student is to teach undergraduate labs and/or discussion sessions. The chemistry department at the University of Southern California (USC), Los Angeles, CA. presented a unique opportunity for its graduate students as ‘Burn Teaching Fellowship’. The fellowship is awarded to one graduate student each semester who is interested in pursuing undergraduate level teaching as a fulltime career. I was awarded with the fellowship for the Spring 2016 semester for ‘Introduction to Organic Chemistry’ (Chem 322A) class. As a part of it I was assigned a mentor, Dr. Thomas Bertolini, who is also the course instructor for that class. Some of the key responsibilities included lecturing 25% of the course, setting 20% of each exam and holding discussion sessions. It was a great experience for me who wanted to get acquainted with the responsibilities of a full time course instructor.


3D printing activities in the chemistry curriculum made possible through collaboration with a centralized campus-supported innovation (maker) lab

Susan M. Ryan, William T. Grubbs, w[email protected]. Stetson Univ, Deland, Florida, United States

3D printing has emerged in higher education as a reliable and affordable learning technology that empowers users to quickly transform ideas into physical prototypes. Ready access to 3D printing promotes creativity and innovation among students and faculty alike. Within the chemical education community, 3D printing has been utilized by instructors to create realistic models of crystalline and molecular structures that afford students an opportunity to grapple with and better understand important aspects of stereochemistry. 3D printed models often allow student to better visualize geometric subtleties in a structure that may not be apparent when rendered using traditional modeling kits. Chemical educators are beginning to incorporate hands-on 3D printing activities as part of the classroom curriculum. As an example, physical chemistry

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students at Stetson University have recently used computational chemistry software to create optimized molecular structures that were subsequently 3D printed. Activities of this type often make difficult to learn concepts more accessible and can greatly enhance student enthusiasm and motivation for learning abstract material. A more widespread adoption of 3D printing curricular activities across higher enrollment chemistry courses requires a sizable up-front investment in multiple printers that is typically not affordable at the department level. Stetson University has been able to overcome this hurdle through the creation and maintenance of a 3D printing innovation lab, housed in the library, which is available to all academic disciplines. Advantages of a campus-supported 3D printing lab include extended-hours access to multiple printers, the availability of technical support staff, and no worries about printer maintenance. Details about the chemistry and library supported innovation lab collaboration will be discussed. Examples of curricular 3D printing activities carried out by students will be presented.


Lipgloss, jewelry and chemistry: Keeping middle school girls excited about science

Stephanie M. Taylor, [email protected]. Science and Mathematics Education, University of Texas at Dallas, Richardson, Texas, United States

Explore the fun and activities at a chemistry camp for girls. Sponsored by the DFW Local Section, designed by faculty, undergraduate and graduate students, a true community was created for an inaugural group of middle school girls. We will investigate activities that succeeded, and explain the future work behind ones that did not. With theme days such as "All About Elements," "Molecule Madness," and "Kitchen Chemistry," twenty girls got their hands into science over the summer. Art was incorporated whenever possible, resulting in at least one project to take home each day, to encourage students to discuss chemistry with their parents. Parents were given conversation prompts to ask specifically what happened in a day's lesson. With this dual encouragement, qualitative assessments were made of how engaged the participants were throughout the week.


Relation between placement test scores and student outcomes in the introductory chemistry sequence

Jason Gavenonis, [email protected]. Chemistry, Dickinson College, Carlisle, Pennsylvania, United States

Introductory chemistry has acquired a reputation--whether deserved or not--as a "weed-out" course, with as many as a quarter of students not continuing to the second semester. As part of our department's regular assessment cycle, we sought to determine whether pre-enrollment placement testing in math and chemistry were

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effective predictors of success in first-year chemistry courses. As has been extensively observed elsewhere previously, math placement testing showed a positive correlation with student success. This correlation is stronger than with our chemistry placement test, which is used primarily to place students in the one-semester accelerated general chemistry class. The strongest correlation with student success, however, was found with both placement tests combined. This presentation will discuss the design and findings of this analysis and the resultant modification of department placement policy.


Implementation of general chemistry curriculum for police officers

Pong K. Yuen2,1, [email protected], Cheng Man Diana Lau2. (1) University of Macau, Macau, Macao (2) Macau Chemical Society, Macau, Macao

Chemistry is a central science and general chemistry course acts as the foundation subject for all students. The effectivenss of chemistry education is critical to the advancement of scientific literacy of mankind. ESFSM is a public university in Macau established for developing personnel in the security forces. Macau's tertiary chemistry curriculum is rarely discussed and researched. This paper introduces the mechanism of designing and implementing general chemistry curriculum. It studies the characteristics, the objectives, the contents and the learning outcomes for police officers.


CADD Academy - Corporate insight into ad-hoc training opportunities within a chemistry organization

Lewis Whitehead, [email protected]. GDC, Novartis, Swampscott, Massachusetts, United States

Within a large global pharmaceutical company, a wide variety of chemistry software applications may appear to be an embarrasment of riches. However, for a small group of computational chemists, training provided for chemistry software applications can be a signficant drain on productivity, even if the engagement pay-off with medicinal chemistry teams is increased signficantly. By leveraging visits by software vendors to our site in Cambridge, MA, we have initiated a quarterly initiative aimed at bridging the training gap for medicinal and computational chemists of all levels of expertise to access globally available software applications.


Implementation of an undergraduate chemistry education certification program

Emily L. Atieh2, [email protected], Darrin M. York1. (1) Rutgers University, Piscataway, New Jersey, United States (2) Chemistry and Chemical Biology,

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Rutgers, the State University of New Jersey, New Brunswick, New Jersey, United States

Peer instruction has seen major growth in higher education over the past decade. Large gateway courses in particular use peer instruction to maximize their greatest resources - their own students. In our Rutgers General Chemistry courses, we host the Teaching Internship program – a for-credit class that provides interns with basic pedagogical training and ample opportunities to apply what they have learned to their own learning sessions with students. Interns not only hold traditional learning sessions, such as office hours and workshops, but they also utilize our latest online instructional technology in order to extend their reach and broaden their skills. They are asked to continuously reflect on their experiences and revise their methods, thus working towards their own personal development. This past year, we launched a new certificate program in chemistry education, which begins with a formal pedagogical training course as a pre-requisite to the teaching internship, and concludes by having students serve as solo teaching assistants for our largest undergraduate chemistry lab course. Typically, the focus of our studies in chemistry education is to monitor the students who are at the receiving end of our peer instructors; the goal of this study, however, is to monitor the gains of the interns themselves in regard to academic standing, teaching methods, and attitudes towards learning.


Exploring learning strategies in a large lecture general chemistry course

Tara S. Carpenter, [email protected]. Dept Chemistry, UMBC, Baltimore, Maryland, United States

Numerous studies have shown that active learning, even in a large lecture course, is more beneficial to student learning than a traditional lecture. Despite the increasing use of active learning, many students still may struggle to pass the course. Research on the teaching of metacognitive learning strategies to students suggests that it can improve their overall performance and increase class averages, even if the first exam doesn’t go well. In this work, a first semester general chemistry course taught in an out-of-sequence semester was investigated to determine the effect of teaching metacognitive learning strategies to students in a flipped class of 320 students. A comparison was also made between students who were taking the course for the first time and those who were repeating the course. The mixed-method investigation utilized surveys on student learning strategies. Results of the survey were compared to exam averages based on student response. Small focus groups (4 – 6 students) were utilized to deepen the understanding of student attitudes and their approaches towards learning. The results of the investigation will be presented.


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Establishing a foundation of acid-base concepts in general chemistry using an interactive online module

Kelly Gilmore, [email protected], Tara D. Todd. Chemistry, Vanderbilt University, Nashville, Tennessee, United States

During General Chemistry 2, the concepts of equilibrium and acids and bases are topics that are covered sequentially in the course. Although these topics utilize the same underlying principles, students often struggle to grasp the connection between the two topics. A common theme among these topics seems to be that students may be able to come to the right answer for a problem, but cannot explain why that answer is correct. This lack of understanding presents itself in later chemistry courses, when students are asked to apply the acid base concepts learned in general chemistry. In this project, we developed an interactive online module that lets students review the fundamental concepts of acid base chemistry as they relate to equilibrium. Students were exposed to small amounts of video lecture material outside of class and then were given the opportunity to self-assess their own understanding. Both formative assessment questions as well as an interactive simulation were utilized in this module. The formative assessment questions were used to help students assess their own understanding, while the interactive portion of the module was used to aid in student engagement. Students’ scores on clicker questions in class were compared to those from a previous year to determine the efficacy of the module in aiding student comprehension. Students were also given a post module survey to assess their attitudes about the helpfulness of the module.


Development of an inorganic chemistry lab at a pui

Andrew G. Eklund, e[email protected]. Alfred Univ, Alfred, New York, United States

Inert atmosphere techniques, inorganic syntheses, materials syntheses, and characterization and monitoring of organometallic reactions are critical aspects of an upper level inorganic laboratory curriculum, even when equipment and spatial considerations are limited. In this course, upper level chemistry students perform air-sensitive syntheses of chromium (II) acetate, copper (I) chloride, and nickelocene using inert atmosphere equipment such as the Schlenk line, the glove bag, and the glove box. Students analyze the kinetics of ring-closing olefin metathesis of 1,7 octadiene using gas chromatography/mass spectrometry and synthesize advanced materials ranging from dimethylsilicone to thermatropic liquid crystals.


Lab sequence and lab-based projects in a course on fundamentals of organic chemistry and biochemistry for undergraduate biomedical engineering major

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Sara Alibeik, [email protected]. Department of Sciences, Wentworth Institute of Technology, Boston, Massachusetts, United States

This work describes the lab sequence and lab-based projects designed and developed for a foundation course in organic chemistry and biochemistry at Wentworth Institute of Technology in the past three years. The course was specifically geared towards junior biomedical engineering students who had taken one semester of chemistry and one semester of biology prior to taking this course. The lab sequence was developed to introduce the key techniques in organic chemistry and biochemistry relevant to biomedical engineering field (15% of final grade). In organic chemistry part of the labs, techniques such as gas chromatography, organic synthesis, polymer synthesis and polarimetry were presented. In the biochemistry part of the labs, selected applications of biochemistry techniques in medical field such as enzyme-linked immunosorbent assay (ELISA) and enzyme catalysis were addressed. For the lab-based project portion of the course, students worked in groups of 3 or 4 on different topics (15% of final grade). The project topics offered were related to cancer diagnostics, cholesterol gene detection, protein purification and PCR-based fingerprinting. The project labs were conducted in the last three weeks of the course. Students presented their findings to the class in an oral or a poster presentation format. Project evaluation involved four components: a review paper submitted prior to the labs, execution of experiments, final presentation and peer evaluations. At the end of the semester, students were asked to submit statements of self-reflection on their learning experience in the labs and the project. These statements and individual feedback from students suggested that students’ learning experience was enhanced through the use of project based labs, instrumentation labs, and labs related to real world context.


Physical organic at a primarily undergraduate institution

Jason F. Fuller2, [email protected], Mary E. Railing1. (1) Wheeling Jesuit University, Wheeling, West Virginia, United States (2) Chemistry, Wheeling Jesuit University, Wheeling, West Virginia, United States

Offering and maintaining advanced/special topics chemistry courses at small, primarily undergraduate institutions (PUI) presents a unique set of intellectual and logistical challenges. PUI chemistry departments often have a limited number of majors resulting in the upper level core chemistry curriculum being offered on an alternating yearly schedule, meaning that some third and fourth year students will not have the prerequisite core courses. Additionally staffing, i.e. workload distribution, for advanced courses can be a challenge for PUI chemistry departments. For the spring 2016 semester the Chemistry Department at Wheeling Jesuit University offered Physical Organic Chemistry as an advanced topics course. This course was team taught by the resident physical and organic chemist. The course met for two 50 minute lecture periods and one 3 hour lab period weekly. This poster will present the course design and outcomes as well as those challenges both expected and unexpected.

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Phone a Friend: Relieving stress while maintaining desirable difficulties in an organic chemistry classroom

Kerry A. Pickin1, [email protected], Christian M. Paumi2. (1) Chemistry, Centre College, Lexington, Kentucky, United States (2) Chemistry, Eastern Kentucky University, Richmond, Kentucky, United States

In the organic chemistry classroom, encouraging students to solve intentionally difficult problems in front of the class with little to no preparation offers students the opportunity to struggle with the material and deepen learning; however, it often produces high levels of anxiety and stress that can suppress learning and stifle the learning community within a classroom. By offering students the opportunity to “phone a friend” and complete the task collaboratively, students gain a sense of relief and camaraderie while the instructor maintains the level of desirable difficulties designed to enhance learning. The application of this process of incorporating both desirable difficulties and collaboratively learning is challenging but provides student with a comfortable, enriched learning environment that promotes both student engagement and deep learning.


Lab demonstration of the kinetics for the hydrogenation of 1-octene

Dana C. Haagenson, [email protected]. University of Wisconsin-Marshfield/Wood County, Arpin, Wisconsin, United States

A series of 1-octene hydrogenations catalyzed by Pd/C are performed by the instructor. The results are presented to the class and discussed. The experiments and discussion will be presented.


Microwave assisted synthesis and characterization of isatin-derivatives to yield substituted quinolone-4-carboxylic acids

Fidelis Manyanga, Mustafa Yatin, [email protected]. Chemistry and Physics, Salem State University, Salem, Massachusetts, United States

Previous studies suggest that halogen or alkyl group containing Isatin, (1H-indole-2,3-dione), and its derivatives can be used for the synthesis of a large variety of substituted quinolone-4-carboxylic acids. These heterocyclic medicinal agents, display a broad spectrum of biological properties, such as antiviral, antifungal, antibacterial, and other inhibitory activities. Microwave irradiation is considered as an alternate greener source of heating. This improves the efficiency of the reactions and reduces the reaction time. In this study, a simple microwave assisted Pfizinger reaction of 5-Chloroisatin, (5-

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Chloro-1H-indole-2,3-dione), with potassium hydroxide and specific ketones are investigated. In this continuing project, the isolated products are washed, purified in silica gel column, recrystallized, and characterized by TLC, 1H-NMR, FT-IR, and UV-Vis spectrophotometry. The green aspects of reactions are evaluated in terms of conventional green chemistry metrics such as atom economy, effective mass yield, and e-factor. Future studies include the use of the substituted quinolone-4-carboxylic acids as starting materials for the synthesis of a broad range of heterocyclic compounds and as substrates for drug synthesis. Molecular docking approaches for drug discovery will be used to model the interaction between isatin derivatives and various proteins/enzymes at the atomic level. Our preliminary studies indicate that this integrative experimental method is versatile, safe, economical and capable of being complemental to routine experiments of an undergraduate organic chemistry laboratory equipped with basic set-up.


There is homotopy in addition to enantio- and diastereotopy

Donald D. Clarke, [email protected]. Cemistry, Fordham Univ, Bronx, New York, United States

Succinate dehydrogenase [SD][EC1.3.99.1], a key enzyme in the Krebs tricarboxylic acid cycle, catalyzes conversion of succinate [butanedioate] to fumarate [E-butenedioate] and is competitively inhibited by malonate [propanedioate]. This reaction is stereospecific. However SD cannot distinguish the carboxylate groups of its substrates which presents a puzzle for students. These are homotopic, while the Hs of the methylene groups are enantiopic and distinguishable by the enzyme. Malonate is bound to the same active site as succinate, thus it is bound in an eclipsed form. Fumarate cannot adopt this form therefore there is a strong driving force to release it from the active site of this enzyme. Accordingly, succinic anhydride [SA] is a useful model for explaining the stereochemistry of this reaction. SA shows a single resonance at 3.02 ppm in its 1H NMR spectrum and two in its 1H decoupled 13C spectrum. The 1H coupled 13C spectrum allows observation of the coupling constants of the geminal and vicinal protons. The J values can be measured with greater resolution and sensitivity in the 13C satellites of the 1H spectrum. If SA reacts with ethanol or other nucleophile the symmetry is broken; the carbonyl as well as the methylene groups give individual 13C and 1H signals.


Illustrating medicinal chemistry through an interactive demo: The Drug Discovery Game

Brian F. McGuinness1, [email protected], James R. Merritt2. (1) Adjunct Professor of Chemistry, The College of New Jersey, Ewing, New Jersey, United States

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(2) NJ Center for Science, Technology & Mathematics, Kean University, Union, New Jersey, United States

An engaging, interactive demonstration of the methods used in modern medicinal chemistry has been developed. Students (playing the role of medicinal chemists) are given seed capital money and challenged to invent a small molecule pharmaceutical starting from a Velcro-equipped scaffold and Velcro-equipped molecular fragments. The teacher (playing the role of a biologist assaying compounds) provides logical feedback after each student’s guess that guides the student toward the solution. The Drug Discovery Game, intriguing at both college and high school levels, launches discussions of such topics as the methods of modern drug invention, the cost of pharmaceuticals, organic synthesis, molecular structure and design, and structure-activity relationships.


Greener extraction and analysis of medicinal plant compounds: A teaching module for undergraduates

John de la Parra1, [email protected], Caroline Webb2, Suraya Foster1, Julian Stanley1, Brandon Dale3, Carolyn W. Lee-Parsons2,1, Vaso Lykourinou1. (1) Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts, United States (2) Chemical Engineering, Northeastern University, Boston, Massachusetts, United States (3) Chemistry, Brown University, Providence, Rhode Island, United States

Our group has developed a 4-part undergraduate chemistry laboratory module that exposes students to a greener method for the extraction and analysis of pharmaceutical compounds from a medicinal plant. The Madagascar Periwinkle is well known for its production of valuable pharmaceutical alkaloids and can be obtained from most

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commercial greenhouses. We have optimized an instructional protocol for extracting alkaloids from mature leaves that successfully replaces dichloromethane with cyclopentyl methyl ether, a greener solvent. As a pedagogical exercise in the principles of green chemistry, students perform extractions with both solvents for comparison. Using Dragendorff’s reagent, we introduce the concept of the qualitative assay. Each fraction of the extraction procedure, as well as appropriate controls, are tested for the presence of alkaloids. Thin layer chromatography is performed with various greener solvents to optimize resolution of major alkaloids components, as well as to illustrate fundamental principles of chromatography to the student. Finally, a method is described for performing supercritical fluid chromatography as a greener technique than traditional HPLC to separate and quantitate the alkaloids present in the extract.


Development of extraction methods for active compounds in botanical species

Lexis Schue1, [email protected], Rachel Miller1, Edmir O. Wade2. (1) University of Southern Indiana, Evansville, Indiana, United States (2) Dept of Chemistry, University of Southern Indiana, Evansville, Indiana, United States

Often referred to as “traditional medicine”, herbal remedies are used worldwide for various ailments. These herbal remedies often seem eccentric to many in the western world who rely heavily on pharmaceuticals. However, many of the pharmaceuticals used today were extracted from some of the most fundamental herbal therapies. From aspirin, which was derived from willow bark, to fungus-derived lipid-lowering agents, a large percentage of the western world’s pharmaceuticals began as herbal remedies. The research being conducted for this project will focus on refining techniques to extract the chemicals from these herbal therapies. Separation techniques will be used to produce an organic and aqueous layer. Techniques such as Nuclear Magnetic Resonance, Mass Spectroscopy, Infrared Spectroscopy, and High Performance Liquid Chromatography will be utilized to examine the organic layer. These methods will then be analyzed to determine which is best-suited for extracting the active ingredients from the herbal remedy. After the method is refined, herbal remedies from different parts of the world will be studied in a future project.


Organic farming and analytical chemistry: A research partnership for chemistry students

Sarah K. St Angelo1, [email protected], Jennifer Halpin2,3, Rebecca E. Connor1, Amy E. Witter1. (1) Chemistry, Dickinson College, Carlisle, Pennsylvania, United States (2) College Farm, Dickinson College, Carlisle, Pennsylvania, United States (3) Food Studies Certificate Program, Dickinson College, Carlisle, Pennsylvania, United States

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As an outgrowth of Dickinson College's Accelerated General Chemistry course project investigating antioxidants in food, a semester-long partnership has been established between a food-based chemistry course and the Dickinson College Farm. In this 200-level, lab only course, students partnered with Dickinson College’s organic farm to perform research meant to give the Farm additional information regarding produce, soil and field management, and food storage and preservation. “Analysis of Antioxidants and Phytochemicals in Foods” has drawn students from all class years, from undeclared students, to majors in chemistry/biochemistry & molecular biology, biology, and environmental science. The students learned laboratory analytical skills, including HPLC, titration, atomic absorption spectroscopy, and colorimetric analysis, which helped them develop their own research questions related to the College Farm. In an intentional feedback mechanism, the students’ research proposals and final reports were shared with the farmers so, if they choose, they could use the findings in their own decision-making regarding future activities on the College Farm.




Effectiveness of active learning in an undergraduate analytical chemistry course

Joseph A. Heppert2, [email protected], Mary E. Erickson3, David D. Weis1. (1) University of Kansas, Lawrence, Kansas, United States (2) Office of Research and Graduate Studies, University of Kansas, Lawrence, Kansas, United States (3) Chemistry, University of Kansas, Lawrence, Kansas, United States

There is a critical need for educators to find ways to increase learning and promote retention of students in STEM fields, including chemistry. One of the most promising pedagogical techniques in recent years is the use of active learning, i.e. “flipped” or “hybrid” courses. This study presents both quantitative and qualitative data from a hybrid undergraduate analytical chemistry course at the University of Kansas. In this course students met for one hour, three days a week, which included working in small groups on active learning assignments. In addition, students were given weekly reading assignments from the course textbook and online homework sets using Sapling® to be completed outside of class. Students were given the option to either fully participate in the active learning portions of the course or to have their course grade based solely on exam grades. A two-tailed t test assuming unequal variance revealed a statistical difference between the average exam grades for students who chose to fully participate (N=42, M=89.689, s=8.515) and students who chose to only fully participate in the exam portion of the course (N=10, M=76.515, s=12.894), t(50) = 3.075, p=0.011, α= 0.05. Results from a survey given at the end of the course will also be presented to compare student demographics such as age, gender, major, as well as attitude towards an active learning environment in this course.

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Mass spectrometry of E-Cigarette liquids by headspace analysis: Introduction to mass spectrometry techniques

Eric Knappenberger, [email protected], Corey N. Stedwell, J. D. DeBord. 1st Detect Corporation, Webster, Texas, United States

We have designed an instrumental analysis laboratory experiment in which students identify and quantify volatile flavorings of E-Cigarette liquids by headspace sampling and mass spectrometry. This experiment introduces the student to the processes of identification and quantitation of unknown compounds, as well as Tandem MS data interpretation. The choice of e-cigarette liquids as a matrix brings modern relevance and student interest to the experiment. The method developed for this experiment utilizes small sample sizes and an MMS-1000 (1st Detect, Houston, TX) Mass Spectrometer. In addition to teaching the fundamentals of MS, this experiment is a safe, simple, easy, and inexpensive demonstration of a real world MS application.


Integrating infrared and UV/VIS spectroscopy to model enzyme inhibition in the instrumental analysis laboratory

Anna M. Fedor, [email protected], Thomas Scott. Chemistry, Misericordia University, Dallas, Pennsylvania, United States

This instrumental analysis lab uses infrared and UV/VIS spectroscopy to study the interactions of antioxidant-active green tea polyphenols with digestive enzymes. When in solution green tea polyphenols have been shown to decrease enzyme activity. Student pairs will propose an experiment using given lists of digestive enzymes and para-substituted phenol derivatives. The inhibition of these enzymes will be monitored qualitatively using infrared spectroscopy focused on the O-H and N-H stretching regions at varying inhibitor concentrations. As the concentration is increased, the intermolecular interactions will be observed as changes in peak locations in the infrared spectrum. Quantitative measurements will be carried out using UV/VIS spectroscopy by recording the absorbance with changing concentrations after identifying the λmax of the enzyme. As the inhibitor concentration increases the absorbance values will decrease significantly. Integrating different types of spectroscopy to study a popular biochemistry research topic will demonstrate the relevance and benefits of a comprehensive use of instrumentation.


Peptide mass fingerprinting of egg white proteins

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Lisa T. Alty1, [email protected], Frederick J. Lariviere2. (1) Washington Lee Univ, Lexington, Virginia, United States (2) Washington and Lee University, Lexington, Virginia, United States

Use of advanced mass spectrometry techniques in the undergraduate setting has burgeoned in the last decade. However relatively few undergraduate experiments examine the proteomics tools of protein digestion, peptide accurate mass determination, and database searching, also known as peptide mass fingerprinting. In this experiment biochemistry students digest a protein mixture from egg white using the enzyme trypsin; liquid chromatography electrospray ionization time-of-flight mass spectrometry (LC-ESI-TOF-MS) separates the resulting peptides and determines their accurate masses. Instrument software is used to match these peptides to the sequences of known egg white proteins, obtained from an online source. Students then use online protein database search software to match the peptides to the protein and score the results.


Fluorimetry and biolayer interferometry to evaluate protein expression in an undergraduate biochemistry laboratory

Rebecca E. Connor, [email protected]. Department of Chemistry, Dickinson College, Carlisle, Pennsylvania, United States

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Expression of recombinant proteins in E. coli is an integral part of modern biochemistry. These experiments are challenging in the short time frames of undergraduate biochemistry laboratories. A laboratory exercise is described in which expression of a red fluorescent protein, mCherry-His, is monitored over two hours of expression using fluorimetry and biolayer optical interferometry. This lab is interesting to students because of the use of a fluorescent protein and the ability to see the cells turn pink as expression proceeds. The addition of a six-histidine tag to the mCherry gene enables the use of a Ni-NTA biosensor to detect binding of the expressed protein, giving the students two different measurements of protein expression. An efficient lysis procedure using a commercial reagent is relatively rapid and enables maturation of the mCherry chromaphore.


High throughput discovery: A multidisciplinary approach to translational research & education

Simon Berritt1, [email protected], David Schultz3, Jeffrey Field2. (1) Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, United States (2) Department of Systems Pharmacology and Translational Therapeutics , University of Pennsylvania, Philadelphia, Pennsylvania, United States (3) Perelman School of Medicine, University of Pennsylvania , Philadelphia, Pennsylvania, United States

Several newly developed massively parallel technologies enable the simultaneous analysis of many biological pathways in an academic setting including cancer. Elucidating cancer pathways is an important task carried out by large scale international efforts, however some rare cancers have not been analyzed in depth. Via funding from the Children’s Tumor Foundation, we developed and offered a translational high throughput screening course allowing undergraduates, graduates & research staff to learn and contribute to these important endeavors. Focusing on Malignant peripheral nerve sheet tumors (MPNST) and Schwannomas (neurofibromatosis 1 & 2), the course was split into two phases. Phase 1 included advanced training on high-throughput systems (Chemistry & Biology), synthesis of a simple PAK kinase inhibitor, and lectures on current topics surrounding MPNST & Schwannomas. Phase two allowed the students to carry out independent research projects either within Chemistry or Biology relevant to neurofibromatosis. High-throughput Chemistry allowed students to rapidly synthesize a small library, which was screened against suitable cell lines. Students were also required to grow cell lines for in vitro testing. The data from this course will be used for publication and development of a public database for rare tumors. We expect the course to be a hypothesis engine that generates ideas for further research in NF1 and NF2 and also a resource to test new compounds, cell lines and screening paradigms for other disease states in a pedagogical setting.


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History of chemistry of the people, by the people, and for the people

Carmen J. Giunta, giun[email protected]. Le Moyne Coll, Syracuse, New York, United States

History of chemistry is the repository of chemists' stories. If chemistry is a vast enterprise to which current researchers contribute, then history of chemistry is that enterprise's archive. Historians of chemistry--including individuals trained as chemists, as historians, and sometimes as both--are its archivists, custodians of the work of chemists past. History of chemistry sheds light on chemistry of the past, and that light can inform and even inspire chemistry in the present and future. Past examples of chemistry of the people, by the people, and for the people will be outlined. I'll take chemistry of the people to mean chemistry applied to human biology, for example Dorothy Crowfoot Hodgkin's elucidation of the structures of biologically important molecules. History of chemistry by the people, I'll take to be history written by chemists in the form of biography or memoir, and I'll focus on work by the prolific writer Carl Djerassi. Chemistry for the people is chemistry applied to societal needs; the career of Fritz Haber includes both nitrogen fixation and chemical weapons, both arguably responding to social or governmental imperatives.


ACS Division of Small Chemical Businesses SCHB is an essential resource for the entrepreneur

Joseph E. Sabol, [email protected]. Chemical Consultant, Marquette, Michigan, United States

If you want to start and run a business in the chemical sector, consider joining the ACS Division of Small Chemical Businesses (SCHB). SCHB’s mission remains “to aid in the formation, development, and growth of small chemical businesses.” SCHB provides relevant programming with resources for and/or featuring start-ups, small, and growing businesses at ACS national, regional, and local section meetings. SCHB members can take advantage of deeply discounted expo booth space at ACS national meetings, be listed in SCHB’s member and business resource directory (www.acs-schb.org), contribute to the semi-annual newsletter, hold office and shape the direction of the division, participate in social media on the ACS Network, Twitter, Facebook, and LinkedIn. SCHB provides member breakfast, lunch, and social/reception at ACS national meetings, scholarships for ACS Leadership courses, and partnership with SOCMA to provide a discounted SOCMA membership. Connect with SCHB in 2016 in Philadelphia and enhance your tool-kit to grow your chemical business.


Chemistry of rubber, it’s more than what meets the road

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Leo C. Goss, leo.[email protected]. Rhein Chemie, Chardon, Ohio, United States

Rubber Chemistry in some circles has been described more of an Art than a Science. It is true that the very beginning of Rubber Chemistry has its roots akin to Alchemy. Alchemists as has been stipulated made attempts to convert base metals to gold or find that universal elixir. Early Rubber Chemists like Charles Goodyear and Thomas Hancock forged similar paths in that they took base saps and tried to convert their inventions into gold. This presentation will attempt to address the fundamental aspects of Rubber Chemistry and the impact on society. Rubber Chemicals can be classified into basic categories. These basic categories are Activators, Accelerators, Vulcanizers (curing agents), Retarders, and Antidegradients. It is the interaction of these Chemicals that provide many of the properties desired by consumers in their products.


Fluorine chemistry of, by, and for the people of the world

Steven H. Strauss, [email protected]. Chemistry, Colorado State University, Fort Collins, Colorado, United States

Linus Pauling once said that "Fluorine... is in a class by itself." It is the most reactive element, yet makes some of the most inert materials, many of which we use to enrich our lives. The F-F bond is the weakest homoatomic bond, yet bonds between an F atom and an atom of most other elements are the strongest single bonds to those elements. It is the 13th most abundant element in the Earth's crust, yet was only the 47th to be recognized as an element and only the 62nd to be isolated in elemental form. Its unique properties impart unusual and useful chemical and physical properties to many of the compounds and materials it forms. This lecture will include a brief summary of the history of fluorine chemistry followed by a discussion of the myriad ways that fluorine chemistry benefits the people of the world, from safely, comfortably, and economically feeding, sheltering, and clothing us, to maintaining our health, to providing clean and abundant energy, to helping provide a clean, stable, and sustainable environment for the generations to come.

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Electronic materials of the people, by the people, and for the people

Qinghuang Lin, [email protected]. MS 6-250, IBM T J Watson Rsrch Ctr, Yorktown Heights, New York, United States

Modern microelectronic chips are made of three types of electronic materials: electrical conductors, semiconductors and insulators. They are the brain of the Digital Age and the engine of the Knowledge Economy. Sophisticated chips power everything from super computers to mobile devices. They also control modern automobiles, medical devices, and communication networks. The ubiquitous chips have fundamentally altered the way people work, communicate, do business, and receive healthcare, education and entertainment. In this talk, I will give a brief introduction of the semiconductor technology and the microelectronic industry. I will discuss select major discoveries or inventions in electronic materials that have made it possible for the ever smaller, faster and cheaper chips for over 50 years. These discoveries or inventions, many made by chemists, have changed the world and improved people’s lives on the Earth.


Chemical reactions and human actions: Teaching and learning as if they are inextricably linked

Peter G. Mahaffy1,2, [email protected]. (1) Chemistry, The King's University, Edmonton, Alberta, Canada (2) King's Centre for Visualization in Science, Edmonton, Alberta, Canada

The purpose of this multidisciplinary symposium is to highlight the many ways in which chemistry touches human lives: Chemistry is a science of the people, by the people, and for the people. Formal and informal chemistry education should play a central role in strategies to communicate to both scientists and citizens those connections. But do we teach chemistry so that the inextricable links between human actions and chemical

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reactions are highly visible and evident to students? Do we place priority in demonstrating those linkages through learning objectives, course outlines, and assessments? If students reflect on their experiences in courses such as the gate keeper general chemistry course, would the way in which chemistry touches their lives and addresses global challenges be one of the top five things they’d highlight? To make these connections more visible and concrete requires both a vision to do so and strategic planning by chemistry educators to overcome the barriers of inertia that may block implementation of that vision. In this talk we will unpack some dimensions of the human activities of learning chemistry, doing chemistry, and benefitting from chemistry that we might highlight more effectively in formal educational contexts for chemistry to become more visible as a science of the people, by the people, and for the people. Provocative suggestions for next steps will be presented.


From drugs to dyes and back: Understanding innovation in the chemical sciences through the history of the Perkin Medal

Jody A. Roberts, [email protected]. Chemical Heritage Foundation, Philadelphia, Pennsylvania, United States

When at the age of 18 William Henry Perkin isolated what would become the first synthetic aniline dye, he incidentally set into motion a nearly an approach to chemical research and commerce that still endures today. His personal achievements – in science and in industry – were celebrated at the 50th anniversary of the discovery of mauveine in 1906 by the Society of the Chemical Industry – America. Since then, each year, SCI America awards a lifetime achievement award to an individual who has demonstrated innovation in chemistry applied to outstanding commercial results. Awardees include some of the most prominent names of the chemical world in across the twentieth and twenty-first centuries, including (in addition to those joining this panel) Leo Baekeland, Charles Chandler, Herbert Dow, Glenn Seaborg, Carl Djerassi, Ralph Landau, Stephanie Kwolek, Gordon Moore, and Robert Gore. What do we learn about changes to the process and products of innovation by exploring the history of this award? What do we learn about where the chemical sciences may be heading? How can we use the experiences of these individuals to better appreciate the specific contexts and contingencies of the innovation process to help us design a more sustainable path forward with and through the chemical sciences? These questions will be the focus of this talk.


CPP-115: A novel GABA aminotransferase inactivator and potential new treatment for epilepsy, addiction, and hepatocellular carcinoma

Richard B. Silverman, [email protected]. Department of Chemistry, Department of Molecular Biosciences, Chemistry of Life Processes Institute, Center for

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Molecular Innovation and Drug Discovery, Center for Developmental Therapeutics, Northwestern University, Evanston, Illinois, United States

An imbalance in the levels of the inhibitory neurotransmitter γ-aminobutyric acid (GABA) and the excitatory neurotransmitter glutamate can lead to convulsions. Inhibition of γ-aminobutyric acid aminotransferase (GABA-AT), the enzyme responsible for the degradation of GABA, increases the GABA levels, which has been shown to produce an anticonvulsant effect. A sharp rise in dopamine release is associated with a variety of addictive behaviors. This dopamine release can be attenuated by an increase in GABA; therefore, inactivation of GABA-AT also has an effect on addictive behavior. Inactivation of a related enzyme, ornithine aminotransferase (OAT) in hepatocellular carcinoma (HCC) has been shown to slow the growth of this cancer. In this lecture the design and mechanism of some of our GABA-AT inactivators will be discussed and how these compounds led to the design and discovery of CPP-115, a potent inactivator of GABA-AT, which has been found to have excellent pharmacokinetic and pharmacological properties for the potential treatment of epilepsy and addiction. CPP-115 also inactivates OAT and has been shown to slow the growth of HCC. A closely related analogue of CPP-115 was identified that does not inactivate GABA-AT but is a potent inactivator of OAT. Enzyme inactivation mechanism studies will be discussed, as well as in vitro and in vivo efficacy and pharmacokinetic results, toxicology studies, and early clinical trial results.


Towards sustainable optoelectronic materials for advanced technologies

Elsa Reichmanis, [email protected]. Georgia Institute of Technology, Atlanta, Georgia, United States

Our educational infrastructure can help promote a global, multidisciplinary culture of sustainability. Examples include i) university wide initiatives, ii) externally funded educational activities, iii) industrial-academic research partnerships, and iv) research in materials chemistries for advanced technologies. Together, these examples demonstrate how academic institutions can enhance their research, education, and service missions through leadership and decision making inspired by the principles of sustainability. This presentation will explore how a focus on sustainability can impact the design and development of all-printed, flexible electronic devices. Such devices present potential low cost alternatives for devices in a range of industries such as health care, security, and energy. We will examine how bio-derived materials might facilitate the development of advanced optoelectronic materials and devices.


What would Sir William Perkin think today?

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Cynthia A. Maryanoff, [email protected]. Baruch S Blumberg Institute, Holicong, Pennsylvania, United States

Sir William Perkin’s discovery of mauveine in 1856 was the beginning of chemical industry. Now, 160 years later what would he think of the pharmaceutical industry? This is an exciting time: medicines impact the quality of life. Delivery of new drugs to patients relies on chemists to eliminate hazardous solvents, reagents and reaction conditions, to provide a synthesis process that can be scaled safely. Examples will be discussed.


Use of exam reflections to assess student examination performance in organic chemistry courses

Andrew G. Karatjas, [email protected]. Science Department, Johnson and Wales University, Providence, Rhode Island, United States

Exam reflections were used to assess examination performance in recent organic chemistry and general and organic chemistry (first semester in a two semester GOB sequence) classes. Self-assessment of study habits and reasons for getting questions wrong were explored to look at factors that influence examination performance. These include student study time, student assessment of sufficient study habits, type of activities used by students, and reasons for missing examination questions.

CHED 100

Grade perceptions in a chemistry program (from non-majors courses through graduate students) - Examination postdictions and the Kruger-Dunning effect

Jeffrey A. Webb2, [email protected], Andrew G. Karatjas1, [email protected]. (1) Science Department, Johnson and Wales University, Providence, Rhode Island, United States (2) Chemistry , Southern Connecticut State University , New Haven, Connecticut, United States

While work has been done in other fields (primarily psychology) investigating self perception of knowledge, limited work in this area has been done in chemistry. We previously reported the presence of the Kruger-Dunning effect at all levels of a chemistry program by looking at student predictions of examination performance. This research continues the study by looking at student postdictions (students make a prediction of their examination grade after completing the examination) of examination performance. Self-reported data in chemistry courses at all levels (from Spring 2013 through Spring 2014) was explored to examine if there is a change in student ability to predict examination performance after completion of an examination. This study also seeks to examine whether there is a difference between the levels of chemistry courses, the types of chemistry courses, and the types of students in the courses (i.e. courses for non-science majors, courses for science majors, courses for chemistry majors, etc...).

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CHED 101

Role of student major in grade perception in chemistry courses

Andrew G. Karatjas2, [email protected], Jeffrey A. Webb1, [email protected]. (1) Chemistry , Southern Connecticut State University , New Haven, Connecticut, United States (2) Science Department, Johnson and Wales University, Providence, Rhode Island, United States

As part of our ongoing analysis of grade perceptions in a chemistry program, exploration into the role that a student’s academic background has on their ability to perceive their own performance in the setting of a science course was explored. The student background was examined by looking at student's majors for those taking undergraduate chemistry courses at all levels over a one and one half year period. This included courses for non-science majors, health science majors, and chemistry courses for science majors. Self-reported data was collected for examinations and analyzed to see if background played a role in the student's self-assessment as it related to the Kruger-Dunning effect.

CHED 102

Pikme: Promoting student participation with an app

Smitesh Bakrania, [email protected]. Rowan University, Glassboro, New Jersey, United States

We invite students to participate in class with, “Does anyone have any questions?” We probe their understanding by asking a specific question during lectures. All in the name of improving student engagement by participation. However, it is common for a limited few to participate and those who do likely skew instructor’s confidence in their teaching abilities. This bias exists because the students who raise their hands are likely the same students who understand the concept in question. To avoid false generalization and actively promote participation, Pikme (an iPhone app) was used to randomly sample the class for conceptual understanding. Pikme was designed to present the instructor with an image-based class list that they can use to pick a students at random. The instructor simply shakes the phone to pick a student to ask a verbal question. Upon responding to the question, the instructor can evaluate the students’ response. The selection algorithm ensures every student in the class has had an opportunity to respond and thus ensuring full participation from the class. While the strategy of randomized selection is not new, there are several additional benefits of using this app. These include the ability to monitor participation, track response quality, and mark absences. The app can also be used to aid active learning exercises by generating randomized pairs or groups. With downloads approaching 20,000 to date, Pikme has been used in several classes by instructors from a wide range of fields, countries, and education levels since its first release in 2010. This talk highlights the key features of Pikme and how it can be used to enhance the learning environment. Most importantly, we discuss strategies to create a

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friendly atmosphere for students who at times can be intimidated by the prospect of being picked at random. Beyond sharing good practices and instructor perspectives, outcomes of a broad survey of students who had experience with Pikme in their classes will be discussed. The student feedback indicates an overwhelming support for Pikme’s use as long as common-sense approaches are embraced. In fact, the students observe an overall improvement in class participation as a potential outcome of integrating Pikme with lectures. These results highlight how traditional lectures can be augmented by technology to yield highly engaging learning environments without the need to overhaul an already functional instructional style.

CHED 103

Designing LEGO activities to help students learn general chemistry topics

Junyang Xian, [email protected]. Chemistry, Drexel University, Philadelphia, Pennsylvania, United States

Many chemistry concepts are difficult for first-year college students. Studies have shown that providing students hands on activities can make them more engaged in class and improve their learning. One technique that has been used to engage students is the use of LEGOs to teach chemistry, such as teaching the students the structure of nano and polymer materials by using LEGO as models. In this study, an activity was developed in which LEGOs were used to model a chemical reaction as a way to help students learn about pseudo-order reaction kinetics. The assembling of LEGOs represented the formation of products; the disassembling of LEGOs represented converting the products back into reactants. The activity was tested in a general chemistry class for chemistry majors during two different years. Clicker questions were posed before and after the activity to determine if there was any change in student understanding of the content as a result of the activity. Student performance on some of the clicker questions improved after the activity, with more students choosing the correct answers and fewer students choosing incorrect answers. A second LEGO activity has been developed to help students understand Le Chatelier’s principle. Results will be presented from the use of this second activity in a general chemistry course (for chemistry majors) and in an everyday chemistry course (open to students from all majors).

CHED 104

Using ‘clickers’ to encode and decode knowledge of bonding, conformation, configuration, (i.e., structure) in organic chemistry. Using ‘clickers’ to encode and decode knowledge of bonding, conformation, configuration, (i.e., structure) in organic chemistry

Steven M. Graham, grah[email protected]. St Johns Univ, Jamaica, New York, United States

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As tools for assessing student knowledge in the classroom, personal response systems (‘clickers’) are becoming increasingly popular. Clickers represent one of the simplest ways to judge the outcome of an active-learning exercise said exercise, especially in a large classroom. One (reasonable) criticism of clickers is that when used to ask multiple-choice type questions (e.g. ‘which of the following are a pair of enantiomers?’) they provide little insight into whether the correct answer was chosen through memorization, luck, or a thorough conceptual understanding of the material. Clickers have been used to assess two problematic issues in the teaching of organic chemistry, namely a student’s ability to draw mechanism arrows (Ruder and Straumanis, J. Chem. Educ. 2009, 86, 1392-1396) and to design a successful synthesis (ibid; Flynn, J. Chem. Educ. 2011, 88, 1496–1500). But mechanisms and synthesis typically are introduced later in organic chemistry; before them comes structure. This talk will outline a way to use clickers so as to dissect a student’s grasp of bonding, conformation, configuration – structure – in organic chemistry. Using the numeric response option of clickers, it will be shown how one can represent a structure digitally, with incorrect answers identifying misunderstandings and misconceptions of structural concepts. This approach is adaptable to a variety of structural concepts; this talk will focus primarily on whether students can interpret condensed structural formulas, identify enantiomers and diastereomers, and convert Fischer projection to chair conformations. This changes completely the nature of the questions that can be asked, turning simple identification questions into robust probes of student understanding ideal for an active-learning environment.

CHED 105

Using digital technology to create student centered collaborative spaces for explaining real-world contexts using organic chemistry

Manashi Chatterjee, [email protected], Solomon Feuerwerker . Chemistry and Biochemistry Department, Hunter College, CUNY, New York, New York, United States

Instructors always try to integrate relevant real-world contexts to engage their students and promote better understanding of organic chemistry concepts. Since organic chemistry is such a fast paced course not all interesting applications can be discussed in class, especially due to time constraints. Narrations of real-world contexts during lecture often only have entertainment value since these topics are not always assessed during exams. It is believed that students enjoy these real life connections and it makes learning meaningful. Textbooks and the Internet (www) provide plethora of examples on application of organic chemistry in real world. Clicker polls conducted during lecture have revealed that less than 50 % of students actually read the medicinally relevant and practically speaking examples in their textbooks in a meaningful way. To stimulate deeper level of interest in these real world topics, including science writing, providing good feedback, peer-assessment and peer-discussions, the use of two digital tools (Wikis and Word press) will be presented. The use of these tools to promote contextually learning of organic chemistry in Organic Chemistry lecture course will be

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discussed. The goals of the project tie in with the Program Level Learning Outcomes: knowledge based and student centered skill based competencies that our Chem. Majors and Minors are required to have when they graduate. Student work in groups and each team has a designated team leader. Each team picks one topic to research; either from the medicinally relevant and practically speaking sections of their organic chemistry textbook or any other news worthy relevant application that interested them. Team Leader posts group work (literature search, writing, videos, case-study) on Wikis or Blogs sites. The collaborative space allows peers from other teams to comment and provide feedback. Examples of student work will be shared. Challenges, best practices and learning curves in use of digital technology in teaching will be discussed. Wikis and Word press blogs will be compared to understand which is better suited for this project. Clicker poll data will be used to show if learning done in cooperative groups using digital platforms produces the more retention. Student attitude towards learning using this method will also be reported.

CHED 106

Incorporation of mobile technology into first-year chemistry courses at Merrimack College

Joanna D. Blanchard, [email protected], Anthony L. Fernandez, [email protected], Brian Provencher, Stephen M. Theberge, Brenda Zwickau. Merrimack Colg, North Andover, Massachusetts, United States

Before the start of the Fall 2015 semester, all first-year students at Merrimack College were provided iPads as part of the Mobile Merrimack initiative. This program has the aim of transforming the Merrimack student experience through the integration of technology in teaching and learning and increased access to interactive and wireless services. In order to take advantage of this new mobile technology, the Department of Chemistry and Biochemistry decided to integrate iPads as much as possible into the first-year chemistry courses. Students use their iPads as classroom response devices, as video authoring tools, and as the interface for a newly adopted laboratory probeware system. Some of the benefits of the iPads are that they allow for instant feedback in lecture and the immediate visualization of data in the laboratory. The successes and challenges of integrating and utilizing this mobile technology will be discussed.

CHED 107

Application of pupillometry in chemistry education research

Josibel Garcia1, [email protected], Melissa Weinrich1, Hannah Sevian2. (1) University of Massachusetts Boston, Boston, Massachusetts, United States (2) Chemistry Department, University of Massachusetts Boston, Boston, Massachusetts, United States

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A great proportion of students encounter difficulties in learning chemistry. This may be because the tasks involved in acquiring new chemistry knowledge and applying that knowledge to solving problems presents insurmountable cognitive load, which is the amount of mental effort used in working memory. The human eye offers an opportunity to observe and study the involuntary reflexes and pupillary responses that result from the brain processing information and emotion. This window into the subconscious can aid in interpreting the mental burden required to process and retrieve information in the brain. Measurement of pupillary responses may permit us to examine how information can be acquired and applied more effectively by students when learning chemistry. Pupillometry studies in psychology have shown that pupillary responses may indicate brain processing and mental activity, including cognitive load. Based on item statistics, items anticipated to require basic vs. complex mental processes were selected from the Chemical Concept Inventory (CCI), which is a tool to assess students’ conceptual understanding in general chemistry. Using an eye tracker, pupillometry was applied to measure mental activity in participants (N=25) just before they began a first-semester general chemistry course. In addition to this measurement, we replicated Klingner’s (2010) pupillometry study with simple mental tasks (memorization and vigilance) to validate pupillometry metrology. Pupillary responses were analyzed to uncover patterns in the cognitive load required to complete the chemistry tasks. In particular, the correlation between pupil diameters and problem complexity was examined. Since working memory and mental function have limited capacities, the larger objective of the project was to use pupillometry to optimize learning with the least cognitive burden during chemistry lessons, so that students can assimilate chemistry material in the classroom efficiently and effectively. Implications for the usage of pupillometry as a measurement method in chemistry education research will also be discussed.

CHED 108

Gaze transition entropy: Assigning a measure of randomness to distinguish participants' levels of understanding of chemistry word problems

Philip Nahlik1, [email protected], Patrick L. Daubenmire2. (1) Chemistry and Biochemistry, Loyola University Chicago, Chesterfield, Missouri, United States (2) Dept of Chemistry, Loyola University Chicago, Chicago, Illinois, United States

Recent eye-tracking studies have included analyses of gaze transitions between areas of interest (AOIs). This project sought to summarize gaze transition data by assigning a measure of randomness with a modified Shannon's entropy calculation through the use of OGAMA and Excel software for individual student and instructor participants who solved chemistry word problems. The entropy measures were graphed versus scores on a Group Assessment of Logical Thinking (GALT) survey to analyze if the randomness of gaze patterns could be used to predict levels of understanding and logical thinking in student participants. The analyses so far did not yield a definitive test to distinguish levels of logical thinking or understanding. However, suggestions will be given to improve future data analysis methods involving the equal or unequal placement of AOIs, entropic or stationary distribution measures, and the physical layout of the

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stimulus slide. Interpretation of these measurements in terms of theories of expertise and student problem-solving strategies will be briefly discussed.

CHED 109

Investigating preservice chemistry teachers’ references for macroscopic, symbolic and submicroscopic levels representing for chemical equilibrium via eye tracking

Sule Korkmaz Yavuz, [email protected], Sevil Akaygun. Secondary School Science and Mathematics Education, Bogazici University, Istanbul, Turkey

Three levels of representation; macroscopic, submicroscopic and symbolic and the transformations among them are important for understanding chemistry. Visualizations that integrate representational levels have been used to promote conceptualizing the chemical phenomena. However, if the learners could get full benefit from the visuals that they are looking at is still a question to be investigated. The present study aims to investigate how the preservice chemistry teachers integrate and explain three representational levels for the concept of chemical equilibrium. In this respect, the preservice chemistry teachers’ eye movements were examined while they were watching a dynamic visualization and answering screen questions about chemical equilibrium. The visualization used in this study is a VisChem (http://www.vischem.com.au) visualization, which presents the process of chemical equilibrium at three representational levels simultaneously. Voluntarily participating preservice chemistry teachers were divided into two groups considering a departmental course in which they specifically learn how to represent the basic chemistry concepts like states of matter, physical and chemical composition and solubility at three representational levels. The eye movements of the preservice teachers who took this specific course were compared with those who did not take. Data were collected quantitatively through eye tracker as well as qualitatively through think aloud protocols because the eye tracker data could demonstrate where the participants focus on, rather than why. For this reason, preservice chemistry teachers’ eye movements showing how they transfer between different representational levels while answering the questions were recorded. In addition, they also explained verbally what they thought and how they reached their answers while watching the visualization. So the eye tracking data were enriched by the reasoning of focus. For the data analysis, the fixation time on each representational level was compared to reveal which representational level the preservice chemistry teachers stare at mostly. Furthermore, the integration of representational levels was analyzed regarding the participants’ scanpaths that they constructed to reach an answer for screen questions. The patterns of scanpaths were compared. The similarities and differences between the

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fixation time and scanpath of the two groups of preservice chemistry teachers will be discussed.

CHED 110

Authorship and publication ethics in undergraduate research partnerships

Aneri C. Pattani, [email protected], Patricia A. Mabrouk, [email protected]. Department of Chemistry & Chemical Biology, Northeastern University, Boston, Massachusetts, United States

Nine research-active STEM faculty-undergraduate research student teams from a research university were interviewed to explore faculty and student understanding and experiences related to responsible authorship and publication practices, as this is a core topic in the federally mandated responsible conduct of research (RCR) curriculum. The interviews revealed that none of the students had received formal training in responsible authorship and publication practices. Many had received no informal training and consequently had questions about authorship and authorship practices. The students’ confusion is reflective of the uncertainty on authorship standards among the faculty members, who held many different views. Delegation of authorship decisions to graduate students appeared to be a common practice. Though faculty espoused definitions of authorship based on contributions (intellectual and material) and writing, many appeared to be concerned about time and effort when it came to deciding student authorship. We propose one possible vehicle for RCR training might leverage graduate students as peer mentors to the undergraduate students.

CHED 111

Transforming the organic lab experience: development and implementation of an organic lab module curriculum at a two-year institution

Jason P. Anderson, [email protected], Brian L. Edelbach, [email protected]. Chemistry, Monroe Community College, Rochester, New York, United States

This work discusses the ongoing development and implementation of inquiry-based microscale organic chemistry lab modules at a community college that were originally conceived at a partnering four-year institution. A description of changing from a traditional expository organic chemistry lab curriculum to delivering these novel organic lab modules will be discussed. One of our primary goals in this project was to demonstrate transportability across institutions, which required adapting the macroscale lab modules to fit our microscale lab curriculum. Several exemplar modules will be discussed to illustrate our experiences during this project; specifically focusing on student improvement in traditional organic lab topics and techniques.

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Professional skills: The latent learning outcome of a project based lab

Nikita L. Burrows, [email protected], Suazette R. Mooring. Chemistry, Georgia State University, Atlanta, Georgia, United States

Literature over the past fifteen years has observed an intensified growth in the discussion of inventive pedagogies for the chemistry laboratory. Project Based or inquiry based labs has become one such innovation of recent discussion in the academic world. The primary objectives of these labs are often embedded in the cognitive and psychomotor domains with little attention to the affective domain. Studies have also explored how these objectives resonate with students; however, employers have expressed the need to train students beyond these objectives. Thus, we explored a project-based, Organic Chemistry lab that focuses on helping students build transferable skills. These transferable skills are skills that students can use beyond the context of chemistry. Eighteen participants were interviewed in a semi-structured interview format to collect their perspectives on the Organic Chemistry Lab. Each interview was subjected to open coding and the constant comparison method. The codes were was collapsed into common themes. To that extent, we present the findings of student perspectives on this lab and the alignment of their perspectives with the labs implicit and explicit objectives. We will particularly focus on the transferable skills that students discussed in their interviews.

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Stepwise approach to writing in the organic chemistry course sequence and beyond

Jay W. Wackerly, [email protected]. Department of Chemistry, Central College, Pella, Iowa, United States

This presentation outlines my efforts towards transitioning second-year, organic chemistry students from writing short, informal lab assignments to writing disciplinary specific journal style lab reports and plan to test the efficacy of this approach. The primary emphasis of this approach focuses on building students' rhetorical skills in scientific and technical writing based on established pedagogical precedent. This approach will then be analyzed in the context of ideal writing outcomes for ACS certified chemistry majors. Finally, a generalized rubric for a capstone paper or senior thesis will be presented along with an outline of a research model to collect data on the effectiveness of this approach.

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CHED 114

Integrating innovative polymer chemistry research into the introductory general chemistry two course sequence–fostering STEM interest and retention

Ophelia Wadsworth, [email protected]. Chemistry, Fisk University, Nashville, Tennessee, United States

A National Science Foundation grant was awarded to Fisk University for the expressed purpose of integrating polymer chemistry research into the General Chemistry lab experiment curriculum. The aim was to 1) foster student interest in pursuing chemistry or other STEM disciplines; 2) increase deeper student learning due to this piqued interest; and thus 3) lead to on-time graduation of these STEM majors who pursue STEM careers or post-graduate training in relevant fields. Ten students participated in the initial Chem 113P course in Fall 2015 while the remaining thirty-nine students enrolled in the regular Chem 113 course. All students were taught equivalent laboratory concepts; the only exception is that polymers were integrated in the lab experiments for Chem 113P students. The course lecture differed in that the ten participants were exposed to actual polymer chemistry instruction during one out of three weekly sessions. Laboratory and course lecture performance were assessed via quizzes, homework assignments, oral presentations, tests and exams. The average grades for laboratory experiments and course lecture for Chem 113P students were lower than those for their counterparts in Chem 113. These results may have been determined by the following variables: 1) sample size disparity; 2) course structure; 3) lack of adequate study habits; and 4) understanding of advanced course material. Additionally, it is necessary to assess other students’ performances through more sample sizes in subsequent semesters. It is estimated that an evaluation period of two years would be adequate to assess the success of this endeavor.

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CHED 115

Fuels chemistry for the people - Energy & Fuels Division (ENFL)

Andre L. Boehman, [email protected]. Department of Mechanical Engineering, University of Michigan, Ann Arbor, Michigan, United States

Humans need to make their activities more sustainable to reduce environmental impacts from pollution and from greenhouse gas emissions. Climate is demonstrably changing, as seen in the migration of plant and animal species toward the poles of the Earth, by recession of glaciers and icepacks around the world, and rising global average temperatures. The targets for 2050 greenhouse gas emissions (CO2 equivalent) are shown in Figure 1, and give a clear indication of the magnitude of the climate challenge. To meet this challenge, we need to become more efficient, use greener chemical processes, utilize greener fuels and use fossil energy resources more wisely, and develop and utilize lower carbon intensity forms of energy. To these ends, scientists and engineers who study energy and fuels are developing a wide array of new technologies and expanding the boundaries of our understanding. An example involving catalysis is the capture of CO2 and its conversion back into fuel, thereby reducing the emissions of additional fossil carbon, which can be accomplished by using the energy from the sun. These new fuels are referred to as Solar Fuels. Due to the pressing problems of energy and climate, members of the Energy and Fuels Division (ENFL) division of the ACS are world leaders in research on advanced energy conversion systems and fuel processing, formulation and production. Specific recurring topics include: * Nanomaterials, catalysts and other materials for advanced energy and fuels processes and systems * Developing and applying computational tools for design of energy processes and fuels * Waste to energy conversion * Novel materials and technologies for gas separation, storage and utilization * Conversion, processing and utilization of biomass to fuels and energy * Solar energy conversion and utilization Figure 1. US CO2 Emissions in 2005 and the target for US CO2 emissions in 2050. (Pavlak, A., American Scientist, 2009)

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CHED 116

Energy for the people

Paul R. Robinson, pr.robi[email protected]. Currently Unemployed, Katy, Texas, United States

Without energy, nothing moves or changes direction. In today’s world, when people discuss energy, they tend to think of fossil fuels. Rightly so! In 2014, 86.3% of the energy consumed came from fossil fuels and about 1/3 came from petroleum. We call them fossil fuels because they were formed millions of years ago from the remains of ancient microorganisms. Petroleum has certain advantages. It is liquid at ambient conditions, so it is easy to transport. It has high energy density. It contains thousands, perhaps millions, of organic molecules. Consequently, it serves as the organic source of tens of thousands of chemicals and consumer goods – polymers and plastics, fibers and paints, drugs and cosmetics, baby oil and pesticides, milk cartons and grocery bags – not to mention lubricants, solvents, rubber, asphalt, and fertilizers. Petroleum now plays a central role in economics and politics, and our unabated thirst for fossil fuels impacts the quality of our air, our water, and the earth itself. Due to the tremendous value of petroleum, industry, government, and academia devote significant resources to petroleum-related research. Members of the American Chemical Society Energy and Fuels Division (ENFL) are world leaders in such research. Specific recurring topics include:

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● Developing analytical instruments and techniques for characterizing petroleum, coal, and their products ● Developing catalysts to lower the cost and improve the efficiency of removing contaminants and converting heavy petroleum fractions into higher-value products ● Transforming coal and natural gas into synthetic petroleum via Fischer-Tropsch process and other technology ● Generating petrochemical precursors ● Converting renewable cellulose and plant oils into petroleum alternatives ● Abating atmospheric CO2 ● Accomplishing the above-listed activities while protecting workers and the environment

Figure 1: World energy consumption by type (prepared with data from the BP Statistical Review

of World Energy: 2015)

CHED 117

Nuclear chemistry's role in the 21st century

Graham F. Peaslee, [email protected]. Chemistry Dept, Hope College, Holland, Michigan, United States

The ACS Division of Nuclear Chemistry recently celebrated its 50th anniversary. Born shortly after the very public advent of the nuclear age in modern society it experienced tremendous growth during the initial decades. But this growth was unsustainable, as a combination of events including the end of the cold war, power plant accidents and

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competition from other areas of chemistry led to a reduction in interest in this field as it matured. However, in the past decade the NUCL division of the ACS is one of the few that has experienced real membership growth and there is a palpable excitement in the next generation of nuclear chemists around recent advances in both fundamental nuclear chemistry and its applications across a broad range of related fields in energy, environment, materials and defense. A brief summary of some of these exciting new research avenues in nuclear chemistry will be presented, together with a discussion of nuclear chemistry's impact on society (of the People, by the People, and for the People).

CHED 118

Chemistry of the people, by the people, for the people: AGRO perspective

Kevin L. Armbrust, [email protected]. Department of Environmental Sciences, Louisiana State University, Baton Rouge, Louisiana, United States

The division of Agrochemicals has its genesis from the agricultural industry’s need to provide an abundant food supply for future generations while meeting the increased demands for safer products to both humans as well as environmental systems. The AGRO division was founded in 1969 at the onset of era of Rachel Carlson’s Silent Spring, with the recognition that chemicals developed from or for agriculture must be done in a more sustainable manner. This could only be accomplished through collaborative efforts between chemists, biologists, toxicologists and social scientists working across industry, academia and government. Divisional programing includes regular or “standing” symposia on agrochemical environmental fate and metabolism, environmental analysis, regulation, ecosystem and human risk assessment, discovery synthesis and application technologies. AGRO creates a forum for trans disciplinary and sector intercourse, setting the stage for interdisciplinary collaborations. The membership rosters boast members from major pesticide and fertilizer manufactures, government scientists from agencies responsible for regulating these industries, and academic scientists conducting work within these fields and is cross-disciplinary with the divisions of Environmental Chemistry (ENVR) and Agricultural and Food Chemistry (AGFD). In recent years the scope of the division has expanded to include the biofuels and renewable energy sectors especially as it relates to the use of agricultural feed-stocks as well as molecular biology (biotechnology) approaches to future agricultural chemical development. AGRO has positively impacted regulatory policy development as well as the regulated industry and will continue to evolve as the needs of society and technology change over time.

CHED 119

Improving the environment by committee

Christopher W. Avery, [email protected]. National Council for Science and the Environment, Washington, District of Columbia, United States

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The Committee on Environmental Improvement (CEI) operates at the nexus of science, public policy, and communication with the general public. CEI works to balance the needs of ACS with the reality of the world outside of ACS, and is charged with finding and walking the path connecting the two. The environmental thinkers and leaders that make up CEI have created a unique and particularly effective place for scientists to influence both policymakers and the public discourse. Achieving this requires a unique set of skills that most scientists are simply not trained in. This talk will focus on the work CEI has done to influence the world of environmental policy, with a special focus on climate and energy, as well as the unique individuals serving their fellow chemists, society, and the Society.<!--EndFragment-->

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Keeping it safe for everyone - the Division of Chemical Health and Safety

Frankie K. Wood-Black, [email protected]. Ag., Science and Engineering, Northern Oklahoma College, Ponca City, Oklahoma, United States

No one ever believes when they head out the door in the morning to go to work or school that you will not return due to an accident. Yet, it is possible. The Division of Chemical Health and Safety is focused on making sure that you do make it home and that other than being tired from the day’s labors there are no residual health effects. Safety is everyone’s responsibility. The Division of Chemical Health and Safety is working to provide individuals, students, educators, researchers, developers, manufacturers, and users; information about how to safely work with, develop, produce, use and dispose of materials that may pose various risks. Come and hear how CHAS can help you with your daily tasks.

CHED 121

Discovery and development of LIPITOR® — Would anyone make this molecule today?

Bruce D. Roth, roth[email protected]. TBA, Philadelphia, Pennsylvania, United States

The HMG-CoA reductase inhibitor LIPITOR® (atorvastatin calcium), the largest selling drug in the history of the pharmaceutical industry, was designed and synthesized in 1985 at a time when medicinal chemistry was dominated by QSAR analyses and emerging structure-based drug design. This was prior to the dramatic change in the practice of medicinal chemistry caused by the publication of Lipinski’s Rule of 5, which caused the industry to focus on property-based drug design as a way of controlling ADMET properties. Despite this, one of the key aspects of the selection of LIPITOR® as a development candidate involved development of the relationship between lipophilicity and differential drug distribution to liver and peripheral tissues. This talk will explore the development of the understanding of the tissue selectivity of atorvastatin and other

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HMG-CoA reductase inhibitors in relationship to physicochemical drug properties and place this in the context of the current practice of medicinal chemistry.

CHED 122

Inventing compounds that have novel modes of action against cancer

Ronald Breslow, [email protected]. Columbia University, New York, New York, United States

We built on the surprising finding by Charlotte Friend that some cancers cells turned into normal cells when treated with DMSO, at high molar concentration. By chemical reasoning we eventually invented a compound that did this and was about a million times more potent, SAHA, and showed how it worked. It has been approved and is in human use in the U.S., in Canada, and in Japan. It is still in active use in chemotherapy. Building on this approach, we have now made new compounds that are more selective than SAHA and are promising in cancerous mouse studies performed by my collaborator Dr. Paul Marks. The new biology our compounds elicit has stimulated high activity by many other medicinal chemists.

CHED 123

Green chemistry innovations through the lens of thermodynamics

John C. Warner, [email protected]. Warner Babcock Institute for Green Chemistry, Wilmington, Massachusetts, United States

Nature creates materials of such exquisite structural complexity and diversity that humans may never be able to mimic them. Nature’s elegance is even more astounding when one considers the fact that most chemistry in the biological world is carried out at ambient temperature and pressure using water, for the most part, as its reaction medium. For society to become truly sustainable, the way we manufacture, use and repurpose materials must change dramatically. This presentation will describe John Warner’s entropic considerations of materials design and illustrate their application through recent R&D examples from the Warner Babcock Institute for Green Chemistry. Examples from pharmaceuticals, personal care, construction materials and textiles will be included.

CHED 124

Teach engineering principles on the cheap with concrete

Debbie Goodwin2, Sherri C. Rukes1, [email protected], Andrew Nydam3. (1) Libertyville High School, Libertyville, Illinois, United States (2) Chillicothe high school, Chillicothe, Missouri, United States (3) Science, Olympia High School, Seattle, Washington, United States

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Learn how concrete and other building materials can be used to teach/learn STEM concepts and practices. We will utilize inexpensive, everyday materials to show relevant and engaging ways to involve students in STEM projects/labs. The concrete project involves a series of labs that scaffold into a team competition to design and produce the best concrete puck or beam. Students use inquiry to determine the best ratio of cement and water to make mortar. They design and make cement pucks and beams both with and without the use of reinforcements. The students get to choose the type and placement of the reinforcement materials. A cost factor is assigned to each type of reinforcement so the students are trying to design both an economical and a high strength performing concrete. The students must collaborate and agree on the testing parameters and what constitutes success and failure. Building codes are a great tool for integrating the Common Core into STEM classes. Meter sticks can be used to make simple I-beams to bring engineering into math and physics classes. These and additional activities show the relevancy of science, math and engineering to students' lives and potential STEM careers.

CHED 125

Composites and their uses

Sherri C. Rukes1, [email protected], Caryn Jackson2, Andrew Nydam3. (1) Libertyville High School, Libertyville, Illinois, United States (2) Science, Tolles High School, Columbus, Ohio, United States (3) Science, Olympia High School, Olympia, Washington, United States

The Next Generation Science Standards (NGSS) present both a challenge and anopportunity in terms of integrating material science into the high school chemistry classroom. On the one hand, the standards do not specifically identify composites in the core ideas for chemistry, raising the possibility that they could be left out of a high school chemistry curriculum. On the other hand, the standards emphasize cross-cutting concepts - concepts that bridge the life, physical, and earth/space sciences, as well as engineering, technology and applications of science. Composites also span this bridge, and many material science-based labs or demonstrations are well-suited for inquiry and assessment. For example, comparing the changes in properties caused by different attractions between polymer chains is an idea way to explore, reinforce, or even assess the concept of intermolecular forces. While the changes in physical properties due to the introduction of hydrogen bonds or covalent crosslinks can be measured, they are also obvious enough to be compared without measurements. Other main concepts can be explored and explained using polymers and other material science topics and many existing material science-based lessons can be adapted to fit an NGSS curriculum. The level of exploration and explanation can be adjusted for the course level, using a more conceptual approach for the basic classes, with more detailed inquiry available for the pre-AP chemistry classes. Developing additional materila science lab resources and linking existing high school polymer and other solid state of matter labs to specific

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NGSS performance expectations will promote the long-term integration of material science and composites into high school classrooms.

CHED 126

Cars: A fun and relevant way to teach chemistry

Sherri C. Rukes1, [email protected], Andrew Nydam2, Debbie Goodwin3. (1) Libertyville High School, Libertyville, Illinois, United States (2) Olympia High School, Olympia, Washington, United States (3) Science, Chilocothe High School, Chillicothe, Missouri, United States

Labs and demonstrations will be shared that relate automobiles to the scientific and engineering practices in the new Framework for K-12 Science Education. Content will focus on physical science core ideas as well as applications of science to the everyday world. Correlations to the Common Core standards will be included. Many students have great interest in the automobile but little interest in school or science. We will show how to utilize that interest to engage students in investigating scientific principals. Labs and demonstrations will be shared that are inexpensive, relevant and practical. For example, a series of labs using antifreeze will cover colligative properties, specific gravity (density), specific heat capacity, graphing, brand comparisons, data interpretation, etc. Other labs and demonstrations will include the topics of thermal expansion, phase changes and Charles’ Law. A demonstration illustrating the effect that polymer chain length has on freezing point will be part of a discussion debating the pros and cons of gasoline vs. diesel for fuel.

CHED 127

BioPlastic: Going from synthetic to natural polymers

Sherri C. Rukes, [email protected]. Libertyville High School, Libertyville, Illinois, United States

As society has evolved, the use of plastics has evolved with it. Plastics have been a fundamental material for many of the devices and day to day items that we use. There are many types of plastics around and those various types are plastics are needed for the many different uses that society depends on. With the push to become greener, bioplastics are emerging more and more. This talk will discuss the various components to what makes a bioplastic, how they are made, the difference between compostable and biodegradable, the various types of bioplastics, properties of these plastics, as well as, learn how to make various types of bioplastics. The idea of making bioplastics as an engineering design / inquiry lab will be discussed, as well as, how to actually test the material to see the various properties and show the connection to the crosscutting concepts in the NGSS.ETS1: Engineering Design ETS1.A: Defining and Delimiting an

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Engineering Problem ETS1.B: Developing Possible Solutions ETS1.C: Optimizing the Design Solution ETS2: Links Among Engineering, Technology, Science, and Society ETS2.A: Interdependence of Science, Engineering, and Technology ETS2.B: Influence of Engineering, Technology, and Science on Society and the Natural World

CHED 128

Polymer food chemistry: Have fun with polymer chemistry by making mountain dew’viar

Sherri C. Rukes, [email protected]. Libertyville High School, Libertyville, Illinois, United States

Even wonder how some chefs make those exciting little beads for their meals, drinks and creative deserts? It is all about chemistry. Learn how polymer chemistry and those creative foods are related by learning concepts of various types of crosslinking and other polymer chemistry properties. The session will look at some of the myths that people have about cooking from why vegetables turn brown and soft when overcooked to the exciting new methods of cooking of molecular gastronomy. The talk will focus on the making of Mountain DewVair and see how a fun activity such as Gaviscon Snakes, Mountain Dewvair and others connect food science to the basic chemistry classroom. This activity can be done as a demonstration and lead into a discussion in the classroom to an open ended discovery that could foster an engineering design activity. Other topics of polymer food chemistry will also talk about as extensions. This will get the students excited and see how cooking and baking are related to the chemistry that they learn in the classroom.

CHED 129

Chemistry of toys

Sherri C. Rukes1, [email protected], Edmund J. Escudero2. (1) Libertyville High School, Libertyville, Illinois, United States (2) Summit Country Day Schl, Cincinnati, Ohio, United States

Nationwide, there is a push for more inquiry in the classroom. Toys and polymers are ubiquitous in everyday life. However, the chemistry that underlies these materials is not always presented in a high school chemistry classes. Sometimes this in part reflects the mistaken belief that the concepts that underlie polymer chemistry are too complicated or too advanced for introductory classes. While polymer chemistry principles and concepts can be complicated, they like complicated concepts in organic, inorganic, or physical chemistry, can still be part of any introductory class. The use of toys and polymers are a easy way to teach many chemistry concepts and have many different applications to them. In fact many of the polymers and toys were made / discovered because of space flight or mistake. Indeed, polymers and demonstrations using polymers /toys can sometimes be more useful as examples. For example, polymers as macromolecules

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often have behavior that can be ascribed to entropy effects or using a drinking bird demo to talk about energy transfer and states of matter. Polymers and toys could be used as demonstrations, but at the same token could be use as starting points for more inquiry labs and discussions. Teachers need to think about using the everyday items and grocery store items to put more inquiry into the classroom. This lesson allowed different levels of student research to be incorporated into the high school classroom, challenging all students within their development.

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E-learning in chemistry education: Self-regulated learning in a virtual classroom

Rachel Rosanne Eidelman, [email protected], Yael Shwartz. Science Teaching, weizmann Institute of Science, Rehovot, Israel

The virtual Chemistry classroom is a learning environment for students that are willing to study Chemistry, but have no opportunity to do so at school. The program launched in 2015, and currently, there are 24 active students in the 11th grade and approximately 100 students in the 10th grade. This study investigates and characterizes the virtual learning environment, students' learning profiles and self-regulated learning processes, and tries to establish a connection between these variables. It is claimed that certain skills such as self-regulated learning skills (SRL) help cope with learning and learning progression. Comparing students' SRL skills and strategies whilst studying Chemistry in two different learning environments (face to face classroom and virtual classroom), may result in answering the main questions: what are the needed skills and strategies in order to be successful in the virtual Chemistry environment, and can one predict which student will do well studying in a virtual learning environment based on their SRL profile? Can these skills be developed in a virtual environment using aids, and what aids can contribute to acquisition of SRL skills? Initial results indicate that there are small differences in some SRL categories between control and intervention groups. Significant differences were found in intervention students chat activity over time, and in their ability to answer questions of different levels (categorized by the revised Bloom's Taxonomy). These findings were used to build a student profile and advance understanding of the correlation between course characteristics and the SRL of students in the program. The students are to be followed over a period of 3 years, and the link between SRL and their ability to answer higher level questions in Chemistry according to Bloom's Taxonomy will be investigated. Key words: Chemistry education; E-learning; Virtual learning environments; Self-regulated Learning; High-Order thinking skills; 21st Century skills.

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Exploring the interplay of learning environment, group/individual characteristics, and conceptual learning across multiple contexts in a general chemistry classroom

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Jaime Emberger1, [email protected], Renee S. Cole2. (1) Chemistry, University of Iowa, Iowa City, Iowa, United States (2) Department of Chemistry, University of Iowa, Iowa City, Iowa, United States

Although prior research demonstrates multifaceted benefits of small group work, fewer studies explore how the characteristics of the environment and students influence these benefits. Accordingly, this research explores from a sociocultural perspective how a highly collaborative environment influences students’ learning of chemistry by looking at the interplay of learning context (e.g. lecture, discussion), group, and individual characteristics. We conducted our study in a non-major, first year chemistry course comparing across three contexts: lecture, discussion, and open-ended test questions. Group conversations from two lecture groups and each individuals’ respective discussion group were video-recorded over the semester. Observation transcripts were analyzed and compared with written test responses using multiple analytical discourse frameworks. These frameworks looked at concepts used, discourse moves, and logical processes and helped describe student participation and individual students’ conceptual development across the different contexts. Interviews were further used to probe student perspectives and understand the influence of the features of each context on their learning and participation. Preliminary findings will be presented.

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Does POGIL promote teamwork and problem-solving skills?

Preston W. Stratford2, [email protected], Sara Lemmon2, Damaris Zarco2, Matthew A. Horn1, Heather W. Ashworth2. (1) Dept. of Chemistry, Utah Valley University, Orem, Utah, United States (2) Biology, Utah Valley University, Orem, Utah, United States

Active learning pedagogies generally, and Process-Oriented Guided Inquiry Learning (POGIL) pedagogy specifically, claim to develop process skills while also developing content skills. The relationships between POGIL implementation in a classroom and the development of the process skills of teamwork and problem solving were investigated in a first-semester general chemistry class and general biology class in Fall 2015. We measured the development of teamwork skills using the Comprehensive Assessment Teamwork Measure of Effectiveness (CATME). We found that students find two different attributes desirable in a teammate: “content knowledge” and “contributing to the group.” The only attribute that correlated with final grade in the class was “contributing to the group.” Problem solving skills were measured with the Lawson Classroom Test of Scientific Reasoning. Among other results we were able to see gains in problem solving skills from the Lawson that also correlated with final grade.

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CHED 133

Investigating chemistry and STEM academic peer leaders' professional development related to content knowledge, pedagogical knowledge, and communication and leadership skills

Mary Emenike1, [email protected], Sari Katzen1, Nipa Patel1, Yan Sun2, Stacey Blackwell1. (1) Learning Centers, Rutgers University, Highland Park, New Jersey, United States (2) Graduate School of Education, Rutgers University, New Brunswick, New Jersey, United States

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The Rutgers’ Preparation in STEM Leadership (PSL) Program (funded through NSF DUE IUSE #1432394) provides an opportunity for academic peer leaders (tutors, supplemental instruction leaders, study group leaders, learning assistants, etc.) to participate in advanced training. Through this training, peer leaders develop their communication, leadership, and group facilitation skills. PSL participants also have the opportunity to earn scholarships and partner with faculty conducting educational research. Increasing persistence and retention in STEM fields is essential for building a highly qualified STEM workforce. We believe that the complementary development of content knowledge, pedagogical knowledge, and leadership and communication skills at the college level will contribute to a better equipped STEM workforce because these participants will be prepared for leadership positions that involve mentoring, teaching, and training others. This project at Rutgers University supports the development of a rigorous and structured peer leader training program in STEM disciplines and evaluates the learning gains and skill development of participants. This project also enables the formal collection of data (through concept maps, concept inventories, leadership and communication surveys, writing samples, and observation reports) to investigate these peer leaders' development of content knowledge, pedagogical knowledge, and leadership and communication skills after participating in such positions over the course of one semester, one academic year, or longer periods of time. The evaluation of the PSL Program is intended to help identify specific criteria essential for successful peer leader training and professional development, which can serve as standards for programs within and beyond Rutgers University. This presentation will include an overview of the PSL Program requirements, participant demographics from our first cohort, data from nearly 100 academic peer leaders who have provided informed consent to participate in the research study and who have responded to some assessments, and lessons learned. We will specifically discuss the development of chemistry content knowledge, pedagogical knowledge, and communication and leadership skills for academic peer leaders in chemistry courses, and situate these findings within the broader population of academic peer leaders in STEM disciplines.

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Evaluating the role of visualization tool such as simulation towards students’ conceptual understanding of chemical equilibrium

Bharath Kumar, [email protected]. STEM Education, University of Kentucky, Lexington, Kentucky, United States

The purpose of this study is to answer the driving question, “evaluating the role of visualization tool such as simulations towards conceptual understanding of chemical equilibrium at the particulate level”. Students find chemistry concepts abstract,

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especially at the microscopic level. Chemical equilibrium is one such topic. While research studies have explored effectiveness of low tech instructional strategies such as analogies, jigsaw, co-operative learning, and using modeling blocks, fewer studies have explored the use of visualization tool such as simulations in the context of dynamic chemical equilibrium. Research studies have identified key reasons behind misconceptions such as lack of systematic understanding of foundational chemistry concepts, failure to recognize the system is dynamic, solving numerical problems on chemical equilibrium in an algorithmic fashion, erroneous application Le Chatelier’s principle (LCP) etc. Kress et al (2001) suggested that external representation in the form of visualization is more than a tool for learning, because it enables learners to make meanings or express their ideas which cannot be readily done so through a verbal representation alone. Schnotz integrated model of audio and visual comprehension is used as the conceptual framework to guide the work. Mixed method analysis was carried towards data collection. The qualitative portion of the study is aimed towards understanding the change in student’s mental model before and after the intervention. A quantitative instrument was developed based on common areas of misconceptions identified by research studies. A single group pre (quantitative/qualitative) – intervention - post (quantitative/qualitative) test was conducted with (N=15) undergraduate students who were enrolled in a second semester college chemistry class. Qualitative interviews pre and post revealed students’ mental model or thought process towards chemical equilibrium. Simulations used in the study were developed using the SCRATCH software platform. When comparing pre and post-test scores for (N=15), the average pre and post test scores were 38.2% and 69.1% respectively, yielding a % difference of +30.1. While this % difference is positive, is was also found to be statistically significant. When a correlation was performed, the pre-test and post-test were significantly correlated at the 0.05 level.

CHED 135

Understanding college students' exam process in a general chemistry course

Angela M. Willson1, [email protected], Megan G. Kowalske2,1. (1) Science Education, Western Michigan University, Kalamazoo, Michigan, United States (2) Chemistry, Western Michigan University, Kalamazoo, Michigan, United States

The main way most college chemistry courses assess what a student has learned is through a summative exam. After introductory science courses, such as general chemistry, many students cite poor teaching and disappointing grades in these courses as a reason for dropping out of STEM programs. There has been a lack of qualitative research on students’ experiences of the complete process of taking an exam from start to finish, or the exam process, which includes preparing for an exam, taking an exam, receiving feedback, and responding to feedback after the exam has been graded. Our goal in this exploratory study was to understand the phenomenon of students’ exam process using phenomenographic methods to answer the research questions: How do students think about and approach (1) Preparing for an exam? (2) Taking an exam? (3)

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Responding to results and feedback after an exam? Data was collected through two interview groups. One group was interviewed using a semi-structured interview protocol both before and after an exam and the other was interviewed only after the exam using the same protocol. Qualitative interviews were analyzed using emergent coding to describe students’ experiences of the exam process in their general chemistry course. Interesting themes from this research include students’ perceptions of their confidence, how self-efficacy is a part of students’ exam process, and how students use translation during the exam process to interpret both materials and exam questions.

CHED 136

Educating the new work force demographic in chemistry

Iona Black1,2, [email protected]. (1) OMCA, IM/Yale Medical School, New Haven, Connecticut, United States (2) Chemistry, JMU, Harrisonburg, Virginia, United States

A question that might ask is “Are there differences in classroom responses and performances of undocumented, and documented immigrant students in the chemistry classroom on both the undergraduate and graduate arena?” Although the DACA program allows participation in the educational system, to what extent are the students participating in 2-year, 4-year, and graduate programs? Are there additional concerns for the chemical knowledge usage and job acquisition? What is the potential effect of the Naturalization through Military Service program having on the education of this population? All of the above questions can affect how undocumented and documented immigrant students are viewed not only regarding acceptance in the post graduate educational system but also in the completion of their education in the chemistry arena. The preliminary observations at a representative 2-year, 4-year, and Ph.D. granting institution will be presented.

CHED 137

Validation of a triplex PCR high resolution melt assay for detecting three common food-borne pathogens and comparison to a commercial water test kit

Thomas H. Boise , [email protected], Kelly M. Elkins. Chemistry, Towson University, Towson, Maryland, United States

We describe the specificity and sensitivity of a PCR high resolution melt (HRM) multiplex assay using LCGreen Plus for the detection of Salmonella enterica, Shigella flexneri, and Escherichia coli. A dilution series of each strain grown in LB broth was prepared, DNA was extracted from each and the samples were tested using the PCR HRM assay, which was found to have high specificity and sensitivity for each bacteria strain. The results of the assay were compared to an inexpensive commercial water test kit that was also tested with each dilution. The water test kit lacked specificity and sensitivity as compared to the PCR HRM multiplex assay. The assay was also

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successful in detecting bacteria inoculated in apple cider. Testing the assay with various other bacterial strains is being performed to further examine specificity of the assay.

CHED 138

Using ion mobility spectrometry for detection of trace pesticides

Lauren E. Moskowitz, [email protected], Grace Anne Martin, Liren Yu, Parijat Sharma, Leonard Demoranville. Centre College, Danville, Kentucky, United States

The presence of pesticide residues is consistently among the top reasons for safety violations related to imported fresh produce. We seek to demonstrate the potential of ion mobility spectrometry (IMS) to be a more efficient means of screening produce surfaces compared to the current method, chromatographic separation coupled with mass spectrometry. Using chromatographic separation coupled with mass spectrometry is time consuming, resulting in minimal produce testing. IMS analysis in the field can occur in seconds, providing an initial screening that can more effectively direct laboratory efforts. Our research group has studied IMS response to various pesticides using thermal desorption coupled with dicholoromethane and ammonia dopants. The pesticides tested were the most common on the U.S. Environmental Protection Agency’s list of import violations. The appropriate dopant and optimal desorber temperatures are reported. Additionally, limits of detection, limits of linearity and reduced mobility are reported for each pesticide.

CHED 139

Determination of gallic acid present in juice and tea beverages using high performance liquid chromatography

Margaret de los Santos, [email protected], Julie Leong, [email protected], Soraya Svoronos, Paris D. Svoronos. Chemistry, Queensborough Community College, Bayside, New York, United States

Oxidative processes in our bodies produce free radicals, which may cause harm to our otherwise good health. Antioxidants, such as polyphenols, which are present in beverages inhibit the oxidation of biomolecules. The Gallic Acid Equivalence Method measures the total amount of antioxidants in the wine industry. Gallic acid, which is used as the standard for the measurement of the total antioxidant content, was found to quench free radicals by getting itself oxidized, thereby reducing cell damage. A procedure for the measurement of the total concentration of gallic acid present in various beverages was measured by High Performance Liquid Chromatography (HLPC). A standard gallic acid calibration curve was first prepared and further used to measure the amount of gallic acid present in commercially available tea and juice beverages. All samples were also allowed to be air oxidized for a week to semi-quantitatively measure the decomposition of the gallic acid originally present during that

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time frame. A comparison between various brands of beverages will be presented in addition to highlighting the differences between the drinks.

CHED 140

Determination of the total amount of antioxidants in beverages via the Folin-Ciocalteu method

Julie Leong, [email protected], Margaret de los Santos, [email protected], Soraya Svoronos, Paris D. Svoronos. Chemistry, Queensborough Community College, Bayside, New York, United States

The total phenolic content present in fruit, tea and coffee beverages was determined via the Folin-Ciocalteu method in a way similar to the one used by the wine industry. This procedure uses the Folin’s phenol reagent that oxidizes the polyphenols in the beverages into the corresponding polyquinones. The reduced phosphomolybdate/ phosphotungstate reagent produces a blue color that allows the microscale visible spectrophotometric determination of polyphenolic antioxidants originally present in the beverage. The results were expressed as gallic acid equivalents and the measurements were made using the Beer-Lambert’s Law. This method was extended to several commercially available beverages as well as tea bags and instant coffee samples. A semiquantitative measurement of the antioxidants’ decomposition after seven days was also determined giving an estimate of the percentage of air oxidized decomposition of the polyphenols.

CHED 141

Effect of pH on the spectroscopic properties of several hydroxycinnamic acid derivatives

Morgan Franke, [email protected], Paris Hanson, [email protected], Elmer-Rico E. Mojica. Chemistry and Physical Sciences, Pace University, New York, New York, United States

Hydroxycinnamic acids are a class of aromatic acids and hydroxy derivatives of cinnamic acid. These compounds account for about one third of the phenolic compounds in our diet. Hydroxycinnamic acids are of great interest because they are potent antioxidants. This study observed the effect of pH on the spectroscopic properties (absorbance and fluorescence) of caffeic acid, coumaric acid, ferulic acid and sinapic acid. Computational calculations on absorbance were also carried out and compared with the experimental results. The absorbance and fluorescence spectra blue shifted from pH 3 to pH 7 and then red shifted from pH 7 onwards. Emission intensity was also observed to increase with increasing pH in ferulic acid and sinapic acid. However, caffeic acid, only increased in emission intensity up to pH 10. The emission intensity of coumaric acid decreased from pH 3 to pH 7 and increased and remained the same at higher pH. Theoretical calculations agree with experimental results in

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absorbance where in there is a blue shift from pH 3 to pH 7 and then a red shift from pH 7 onwards.

CHED 142

Comparative analyses of phenol content and antioxidant properties of Philippine tea samples

Jahaira Zapata, jz2[email protected], Morgan Franke, [email protected], Elmer-Rico E. Mojica. Chemistry and Physical Sciences, Pace University, New York, New York, United States

The phenol content and antioxidant properties of the water extracts of seven commercial fruit and medicinal plant based teas from the Philippines were evaluated and compared to one another. The total phenolic content, determined by the Folin-Ciocalteu method varied from 23.2 mg/g (bitter melon) to 91.49 mg/g (pito-pito dried herbal tea) mg of gallic acid equivalent/g dry tea. The antioxidant properties were evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay system, which showed 80% to 100% inhibition or reduction of the DPPH. The 2,2-azinobis (3-ethyl-benzothiazoline-6-sulfonic acid (ABTS) assay was also performed and showed the same results as that of DPPH assay. A general trend in terms of antioxidant activities and total phenol content can be observed, as pito-pito dried herbal tea showed 100% inhibition of both DPPH and ABTS.

CHED 143

Use of molecularly imprinted polymer to improve the analysis of naproxen in environmental water samples

Elijah Jones, [email protected], Rayona Wise, Elmer-Rico E. Mojica. Chemistry and Physical Sciences, Pace University, New York, New York, United States

Pharmaceuticals are continually released into the environment. Because of their physical and chemical properties, they can accumulate in sediments, sludge, and soils, inducing adverse effects in terrestrial organisms. However, due to the very limited methods permitting the detection of these low-level concentration compounds in such complex matrices, their concentrations in environmental samples remain largely unknown. Among these pharmaceuticals are NSAIDs or nonsteroidal anti-inflammatory drugs, a class of drugs that provides antipyretic (fever reducing), analgesic (pain-killing) and anti-inflammatory effects. In this study, naproxen, an over the counter NSAIDs, has been used as the target analyte in the development of sampling pretreatment method using commercially available molecularly imprinted polymer (MIP). The naproxen in environmental water samples was extracted using MIP and then analyzed using high performance liquid chromatography (HPLC). Using the same source of samples, the use of MIP improved the analysis as higher amount of naproxen was found in

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comparison to the analysis made use of Oasis HLB, which is presently used in the analysis of naproxen. A shorter extraction time was also observed.

CHED 144

Binding interaction of nanoceramics (metal oxides) with human serum albumin

Tyler Nolan, [email protected], Elmer-Rico E. Mojica. Chemistry and Physical Sciences, Pace University, New York, New York, United States

Nanomaterials are defined as materials with at least one external dimension in the size range from ~1 to 100 nanometers. The properties of nanomaterials make them versatile materials in various fields of science, ranging from material science, energy, to medicine. This study was conducted because the knowledge on the interactions of nanomaterials with different biomolecules is limited. The interaction of nanoceramics (aluminum oxide, silicon oxide, titanium oxide and zinc oxide) with human serum albumin (HSA)—the most abundant protein constituent of blood plasma— was investigated by various spectroscopic methods (absorbance, fluorescence and circular dichroism). Results showed aluminum oxide significantly changes in terms of reduced absorbance, emission, and CD profile in comparison to the other nanoceramics. Absorbance reduction in samples with silicon oxide was also observed. The nanoceramics also reduced the emission intensity in the samples of HSA. Interestingly, a peak was observed at around 420 nm for zinc oxide and 410 nm for aluminum oxide and silicon oxide as the amount of nanomaterials being added increased.

CHED 145

Analysis of marijuana contamination on currency

Megan E. Malvoisin, [email protected], Karen S. Wendling. Chemistry and Physics, Chestnut Hill College, Philadelphia, Pennsylvania, United States

This research focused on determining marijuana contamination on circulating paper currency (US $1 bills and US $20 bills). Instead of detecting the primary psychoactive ingredient in marijuana, tetrahydrocannabinol (THC), cannabinol was studied. Cannabinol is a psycho-inactive ingredient in the cannabis herb that is also an oxidation product from THC. Cannabinol-d3 (40 μL of 100 μg/mL) was spiked onto each currency sample as an internal standard. The cannabinol was extracted from the bills with 5 mL of acetonitrile. After buffering the solution, a liquid-liquid extraction with 7 mL of hexane/ethyl acetate (9:1) was performed. The organic layer was evaporated to dryness under nitrogen. The dried sample was then reconstituted in ethyl acetate with anthracene-d10 and derivatized with BSTFA-TMCS. The derivatized sample was then injected into the Gas Chromatograph-Mass Spectrometer (GC-MS) where the single quadrupole was operated in Selected Ion Monitoring (SIM) mode. Peak areas were determined for anthracene-d10, cannabinol-d3, and cannabinol. The anthracene-d10 peak area was used to correct for injection inaccuracies as manual injections were

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performed. The cannabinol-d3 peak area was used to determine the percent recovery of cannabinol for each bill analyzed. These percent recoveries ranged from 23.1% to 77.8%. A calibration curve was constructed using cannabinol standard solutions; this curve was used to convert the currency cannabinol peak areas into concentrations. Cannabinol was detected on all three of the $1 bills studied and on five of the six $20 bills studied. After correcting for the percent recovery, the average cannabinol detected on the $1 bills was 115 ng/bill while the average cannabinol detected on the $20 bills was 68.3 ng/bill. While additional currency samples need to be studied, this result suggests that lower denominations of currency may have higher concentrations of marijuana residue due to its relatively low cost compared to other illegal street drugs.

CHED 146

Analysis of hyperforin in St. John's wort capsules

Meghan C. Guagenti, [email protected], Karen S. Wendling. Chemistry and Physics, Chestnut Hill College, Philadelphia, Pennsylvania, United States

The goal of this research was to determine the concentration of hyperforin in St. John’s wort capsules. St. John’s wort is an herbal supplement commonly used as an over-the-counter antidepressant. The active ingredients in the herb include hypericins and hyperforin. While hypericins are frequently quantified by supplement manufacturers and the value listed on the product label, hyperforin is not quantified. Because herbal supplements are not regulated by the Food and Drug Administration (FDA) it is expected that the concentration of hyperforin will vary widely in different St. John’s wort supplements. This research focuses on quantifying the hyperforin concentration in five different herbal supplements. Hyperforin was extracted from the capsule’s herbal contents by sonicating the herb in methanol. The temperature of the bath was kept below 28 °C and the extraction was performed in low light conditions to prevent degradation of the hyperforin. The extract was diluted to 50 mL with methanol and filtered using a 0.45 μm PTFE filter. Ten microliters of the sample was then injected into a High Performance Liquid Chromatograph (HPLC) with UV-VIS absorbance detection (270 nm). The column used was a Phenomenex Luna phenyl-hexyl column (15 cm x 4.6 mm with 3 μm particle size). Isocratic elution was performed with a mobile phase mixture of 90/10 acetonitrile (with 0.3% phosphoric acid)/water at 0.6 mL/min. The hyperforin peak areas were converted into concentrations using a calibration curve constructed from hyperforin standard solutions. Five different St. John’s wort supplements were studied: the organic supplements from Wilde Herb and EarthWise Organics and the conventional supplements from Vitamin Shoppe, Solar Ray, and Solar Ray Guaranteed Potency. Overall, the Vitamin Shoppe brand contained the highest percentage of hyperforin per capsule (0.3694% by mass), while the organic brands Wilde Herb and EarthWise Organics contained the lowest concentrations of hyperforin (0.0215% and 0.0199%, respectively). A price comparison was also made, comparing the cost per gram of herb with the percent by mass content of hyperforin. The two organic supplements studied were the most expensive for the least amount of

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hyperforin active ingredient while the Vitamin Shoppe brand provided the best overall value for the most hyperforin.

CHED 147

Self-powered enzymatic biosensor for simultaneous detection of two biomarkers of Parkinson’s disease

Julia Rutherford, [email protected], Gaige VandeZande, Michelle Rasmussen. Chemistry, Lebanon Valley College, Willow Street, Pennsylvania, United States

Parkinson’s disease is a chronic neurodegenerative disorder which affects 1% of the world population over 60 years of age. There is currently no definitive test to detect Parkinson’s disease in patients, thus it is diagnosed through symptoms and patient history. The purpose of this study is to fabricate and analyze a self-powered enzymatic biosensor that has the ability to detect biomarkers of Parkinson’s disease prior to an onset of symptoms. A specific range of uric acid and glutathione levels in the plasma are the two biomarkers that indicate the possible presence of the condition. It has been found that in a patient with Parkinson’s disease, uric acid levels are lower than normal while glutathione levels are higher. Biosensors function by registering the amount of electrons donated or consumed through an electric current, produced by redox reactions that occurs directly on, or near, the sensor. In order to detect the relative concentrations of the desired substances in the blood, two biosensors must be developed that are either enzymatically hindered or exacerbated by the presence of the biomarkers. This study utilized amperometry and cyclic voltammetry to explore the effectiveness of a laccase cathode and an uricase anode, which respond to either the presence of glutathione and uric acid, respectively, resulting in a decrease in current output. The changes in current is related to the relative concentrations of the substances in the blood, allowing the tested plasma to be compared to both healthy and diseased blood.

CHED 148

Micro-Raman for direct visualization of water transport in an individual aqueous droplet

Kalen Sullivan, [email protected], Samuel Braziel, [email protected], Sunghee Lee. Chemistry, Iona College, New Rochelle, New York, United States

The study of water permeability can been used to foster a deeper understanding of the process of homeostasis, which is responsible for the maintenance of stable physiological conditions in the human body. Raman spectroscopy is a well-established technique to obtain vibrational information for structural and molecular determination of the sample and has many advantages including: no need for sample preparation; non-

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contact, non-invasive and non-destructive; and relative insensitivity to aqueous media. Our set-up includes the combination of our highly-configurable microdroplet-based experimental platform with a high spatial resolution confocal Raman microscope. With this, we demonstrated that the Raman intensity and area of the crystallizable solute peak is linearly correlated with the volume of microdroplet, hence allowing us to determine the concentration at which crystal appears, one of important parameters in the isothermal crystallization process. Our method may provide a significant methodological advance in analysis of water transport in an individual aqueous droplet.

CHED 149

First electrochemical, aptamer-based sensor on a carbon surface

Justine Lottermoser, [email protected], Ryan J. White. Chemistry & Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland, United States

Astrocyte cells use adenosine triphosphate (ATP) to transfer signals. This process is suggested as a novel therapeutic target in Fragile X Syndrome (FXS), one of autism’s few known genetic causes. Our aim is to develop a carbon fiber electrode aptamer-based sensor capable of single cell and in vivo measurements of ATP to determine the release mechanism and spatial location of ATP. Aptamers are short nucleotide sequences that select for target analytes and translate binding into an electrochemical signal. Carbon fiber is very robust, enabling sensitive measurements while eliminating background processes like oxygen reduction that plague existing measurements. We are developing the linkage chemistry to covalently attach the aptamer to the carbon surface. Specifically, we have electrochemically grafted several compounds (4-aminobenzoic acid and ethylenediamine) to the surface of glassy carbon electrodes and have found that 4-nitrobenzene diazonium is best suited for further development. To test for successful grafting, we have employed the positively charged hexaammineruthenium (III) chloride (RuHex) as a redox reporter. Using cyclic voltammetry, changes in observed peak current caused by electrostatic repulsion of RuHex with the grafted electrode surface report on the grafting's success. With the attached diazonium, we are now poised to fabricate our aptamer sensors on carbon surfaces.

CHED 150

Multiple uses of analytical chemistry for art and archeological research

Nicolette Coluzzi, [email protected], Randolph K. Larsen. Chemistry & Biochemistry, St. Mary's College of Maryland, St. Mary's City, Maryland, United States

Analytical techniques in chemistry are relevant to many other disciplines such as art history and archaeology. In this project, several experiments were conducted to show how chemistry can assist in overcoming challenges within other disciplines. X-ray Fluorescence (XRF) and X-ray Diffraction (XRD) were used to perform a trace metal

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analysis of paint pigments. Inductively-Coupled Plasma-Optical Emission Spectrometry was used to analyze archaeological copper samples for trace metals. Differential Thermal Analysis (DTA) was used to analyze archaeological ceramics in order to estimate their date of production. The trace metals found in the copper alloy help archeologists identify their point of origin. Lastly, an open source database can be created from the XRF and XRD data to assist art professionals, conservation scientists, conservators in confirming their pigment identification.

CHED 151

Influence of monovalent electrolyte, glucose, and protein concentrations on sulfate conductivity measurements in urine

Jennifer Garcia, [email protected], Michele S. McAfee, Linda D. Schultz, [email protected]. Medical Laboratory Sciences, Tarleton State University, Fort Worth, Texas, United States

Analysis of urine is an essential tool for monitoring liver and kidney function because urine is an ultrafiltrate. Conductivity measurements yield information about the amounts of ionic species, primarily salts, present in a fluid such as urine, and these measurements are easily done using an inexpensive commercial conductivity meter. Sulfate concentrations can also be measured using this device. However, biological fluids, such as urine, are complex mixtures which contain a large variety of potentially interfering substances. Three urine components which could exhibit dramatic concentration changes in common disease states are monovalent salts, glucose, and protein. To study their effects on conductivity measurements of sulfate, a series of artificial urines were prepared containing known concentrations of sodium chloride, potassium sulfate, glucose, and albumin. Sulfate measurements of these solutions were done using conductometric titrations.

CHED 152

Optimizing solvent and extraction techniques for quantifying ambient aerosols

Stacey Dougher, [email protected], L. E. Meade, Kathryn E. Kautzman. Chemistry, Towson University, Towson, Maryland, United States

In this work we investigate the optimum solvent for the extraction of aerosols from quartz filters, and we compare the techniques of sonication and soxhlet extraction. This research could impact the way scientists analyze airborne compounds by providing an ideal experimental procedure for the extraction of these aerosols. Ideal aerosol analysis is beneficial because researchers may be missing certain classes of aerosols during their research simply because they are not performing extractions under the ideal conditions. Solvents were chosen based on their dielectric constants, which corresponds to the polarity of the solvent. Methanol (ε = 32.7), dichloromethane (ε = 8.93), 50:50 dichloromethane and methanol mix, and hexane (ε = 2.0) are used for the

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solvent extraction study. A 50:50 dichloromethane and methanol mix was used for the extraction method study. Sonication extraction is typically performed during short time intervals; therefore, sonication extraction times were 30 min, 1 h, 2 h, and a maximum of 4 h. Soxhlet extraction is usually performed for a much longer interval of time; however, we must also limit the variability of time. Therefore, the soxhlet extraction was performed for 1 h, 2 h, 12 h, and 24 h. Following the extraction, a drying process was performed. This drying process increased the concentration of aerosols in a sample. Extraction efficiencies for both the solvent studies and the extraction methods are quantified utilizing Gas Chromatography coupled to Mass Spectrometry (GC/MS). Then a statistical analysis was performed to determine if there is indeed a statistically significant difference in the usage of various solvents during aerosol extraction.

CHED 153

Detection of specific single soft particles binding to E-AB sensors in real time

Nicholas Vaccaro, [email protected], Ryan J. White. Chemistry & Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland, United States

Electrochemical aptamer-based (E-AB) sensors can be utilized to detect a multitude of different target molecules in a sample. Current methods, however, are limited to ensemble measurements of a large number of target molecules. Conversely, specific single molecule sensing at low detection limits represents a highly sensitive method of detection of analytes in a sample. In this project, I aim to detect Immunoglobulin E (IgE), a protein that is involved with the immune response in the human body, with specific single molecule sensitivity. Nonspecific detection of single IgEs by previous experimental methods involved observing discrete current reductions in real-time at a gold nanodisk electrode due to IgE blocking part of its electroactive surface area. The proposed method, however, involves modifying the electrode surface with a DNA aptamer specific to IgE, in which only IgE collisions and binding will result in similar current reductions due to the blocking of the electroactive surface. Under these conditions, the protein should bind to the aptamer instead of colliding with the electrode surface. Detecting this particular protein with the proposed protocol will show that DNA aptamers can be utilized for specific electrochemical single particle detection.

CHED 154

Preparation and stability of cis-dicarbonylbis(diorganodithiocarbamato)iron(II) complexes

Brett Szeligo, [email protected], Jason Fuller, Norman Duffy, James Coffield. Chemistry, Wheeling Jesuit University, Wheeling, West Virginia, United States

Iron(II) dithiocarbamate complexes are known to be especially stable; however, recent PNMR of our sample of cis-dicarbonylbis(dibenzyldithiocarbamato)iron(II) revealed, in addition to the expected peaks for the iron(II) complex, a broad peak in the range of 24

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ppm. This peak corresponds to the location of the CH2 peak for the corresponding paramagnetic Fe(III) complex, thus calling into question the extent of decomposition over time of the numerous other cis-dicarbonyl-bis(diorganodithiocarbamato)iron(II) complexes. Currently, various cis-dicarbonylbis(diorganodithiocarbamato)iron(II) complexes have been synthesized and their stability investigated using thermogravimetric analysis (TGA) and PNMR. At ambient temperature, traces of the corresponding paramagnetic tris(diorganodithiocarbamato)iron(III) have been found for some derivatives, indicating possible room temperature decomposition of Fe(II) to Fe(III) or contamination during preparation. Parallel TGA studies have indicated a variety of paths for thermal decomposition, involving simultaneous or step-wise loss of carbon monoxide, leading to intermediates of varying thermal and kinetic stability. These observations will be discussed, along with the implications of the effect of the organic substituents.

CHED 155

Synthesis and interactions between fmoc protected monomer and DNA via spectroscopy

Allyson Farrier, [email protected], Paige E. Sheridan, [email protected], Lauren A. Levine. Physical Sciences, Kutztown University, Kutztown, Pennsylvania, United States

Tert-butyl {N-[2-(N-9-fluorenylmethoxycarbonyl)aminoethyl]-N-[2-(4-pyridyl)-acetyl]amino}acetate (Fmoc-aeg(Py)-Otbu or pyridine monomer) was synthesized by adding 4-pyridylacetic acid and ethlyene dichloride (EDC) to tert-butyl N-[2-(N-9-fluorenylmethoxycarbonyl)aminoethyl]glycinate hydrochloride (Fmoc-aeg-OtBu or backbone) and was further purified using column chromatography. The structure of the pyridine monomer was confirmed using 1H, 13C and 2D nuclear magnetic resonance (NMR) spectroscopy experiments. Fluorescence and absorbance spectroscopy was utilized to observe the interactions of the monomer and a 24 base pair duplex strand of DNA. A monomer solution was titrated with DNA in a phosphate buffer solution to monitor the spectroscopic activity at varying points of saturation. A quenching effect was observed via fluorescence analysis. Due to this observation, a series of fixed volume solutions were constructed at varying degrees of saturation in order to eliminate the effects of dilution from the spectroscopic intensities. The Fmoc-aeg(pyr)-OtBu results were compared to previous research conducted using the Fmoc-aeg-OtBu molecule as a reference. The results were expected to be comparable due to the diminutive size of the pyridine in comparison to the entire molecule. Future studies include the addition of a tethered platinum terpyridine residue to the pyridine monomer to observe intercalation effects with more complex assemblies.

CHED 156

Detection of single Rh nanoparticles using an ultramicroelectrode

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Christopher Peruzzi, [email protected], Scott N. Thorgaard. Chemistry, Grand Valley State University, Allendale, Michigan, United States

In this investigation, we have detected the collisions of individual Pt and Rh nanoparticles (NPs) at a Au ultramicroelectrode (UME) using electrocatalytic amplification. We have synthesized Pt and Rh NPs capped with citrate that were then characterized using electrochemistry and TEM imaging. Optimization of the Rh NP synthesis was done to afford stable nanoparticles to observe their collisions at a Au UME. Nanoparticle collisions were observed using the hydrazine oxidation reaction. The current transients for single collisions at the Au UME showed dependence on cleaning of the electrochemical cell and the UME. Further investigations into the simultaneous detection of either Pt or Rh NPs in a solution depending on the applied potential to the electrode is a goal of this project.

CHED 157

Super-resolution imaging of fluorophores bound to silica-coated gold nanorods

Aaron McLeod, [email protected], Katherine A. Willets. Chemistry, Temple University, Philadelphia, Pennsylvania, United States

Gold nanorods are coated in silica shells of different thicknesses, which are functionalized with fluorophores via a (3-aminopropyl)triethoxysilane linker. We are studying the utility of these samples for super-resolution imaging, in which the fluorescent dye molecules are excited using a laser. As individual molecules relax back to their ground state from an excited triplet state, the intensity and location of each dye molecule is recorded. These data are used to map out the structure of the silica-coated gold nanorod and understand coupling between the plasmon resonance of the rod and the fluorescence.

CHED 158

Interspecies comparison of degradation of a peptide substrate reporter

Allison J. Tierney1, [email protected], Kunwei Yang1, Brooks K. Emerick2, Michelle L. Kovarik1. (1) Chemistry, Trinity College, Hartford, Connecticut, United States (2) Mathematics, Trinity College, Hartford, Connecticut, United States

Peptide substrate reporters are fluorescently labeled peptides that can be acted upon by one or more enzymes of interest. Peptide substrates are generally easier to work with than full-length protein substrates; however, they can be degraded by peptidases. As a result, peptide reporters must be made resistant to proteolysis in order to study enzymes in intact cells and lysates. This is typically achieved by optimizing the reporter in a single cell type or model organism. We are adapting a peptide substrate reporter for protein kinase B (PKB) that was developed in human cells for use in common model organisms. We measured peptidase activity toward the peptide VI-B in D. discoideum,

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S. cerevisiae, and E. coli using capillary electrophoresis with laser-induced fluorescence (CE-LIF). We found VI-B to be stable in D. discoideum (t0.5 ≈ 92 min) and S. cerevisiae (t0.5 ≈ 330 min), but less stable in E. coli (t0.5 ≈ 33 min). Using compartment-based modeling, we were able to determine quantitatively how the peptide fragments formed due to peptidase activity. For example, we found VI-B reporter fragments form primarily from the full-length parent peptide with slower degradation of longer fragments to form new fragments. This data set suggests VI-B is sufficiently stable for PKB assays in D. discoideum and S. cerevisiae while also demonstrating the potential utility of compartment-based models in peptide substrate reporter design.

CHED 159

Tracking PKB activity during Dictyostelium development using a peptide reporter

Kunwei Yang, [email protected], Allison J. Tierney, Michelle L. Kovarik. Chemistry, Trinity College, Hartford, Connecticut, United States

Protein kinase B (PKB) is an enzyme that assists cells to proliferate under stressful conditions. In human cells, aberrant PKB activity is implicated in many cancers, making PKB an important target for further research. We are studying PKB in Dictyostelium, a social amoeba that has highly conserved protein kinase B signaling pathways similar to those in human cells. In Dictyostelium, PKB is activated when cells are under nutrient-poor conditions. To activate PKB in the laboratory, the cells are starved to initiate the development cycle and pulsed with a signaling compound, cAMP, as the first messenger. A fluorescently labelled peptide reporter, VI-B, is a peptidase-resistant synthetic substrate of PKB that can be utilized to measure the activation of PKB by capillary electrophoresis with laser-induced fluorescence (CE-LIF). Although VI-B was developed in human cell lines, we are validating it to use in Dictyostelium. Though background phosphorylation occurs in vegetative control cells, the data suggest that PKB is activated by cAMP pulsing and the phosphorylation by PKB is specific to development. Physiological, genetic and pharmaceutical control experiments are in progress to confirm the specificity of the peptide reporter for PKB.

CHED 160

Determining the total amount of oxygen consumption in effluent via carbonaceous biochemical oxygen demand (CBOD) and biochemical oxygen demand (BOD)

Julie Leong1, [email protected], Faye Jacques2, Panayiotis Meleties3, Paris D. Svoronos1. (1) Chemistry, Queensborough Community College, Bayside, New York, United States (2) New York City-Division of Environmental Protection, Wards Island, New York, United States (3) Chemistry, York College, Jamaica, New York, United States

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Water from showers, rain, melted snow, and sidewalk washing travels into a whole new world through the remarkable systems of pipes in the New York's City sewer system, DEP (Department of Environmental Protection). The DEP is a wastewater treatment plants that removes most of the pollutants from wastewater before being released. One of the most commonly measured constituents of wastewater is the biochemical oxygen demand (BOD) defined as the amount of dissolved oxygen required for aerobic microorganisms (found in sewage) to decompose the organic matter in the wastewater. This value measures the degree of pollutant by identifying the decrease of dissolved oxygen the bacteria used to survive and consume the waste. If more oxygen is consumed than produced, DO (dissolved oxygen) will decrease and some aquatic life forms will weaken, migrate to a different location, or die. This test is used by government agencies to determine how efficient plants are and how effluent (released water from treatment plant) will affect receiving water. Carbonaceous biochemical oxygen demand (CBOD) follows the same procedure as BOD but the nitrifying bacteria in the sample are inhibited. Nitrifying bacteria consume nitrogenous materials (compounds with reduced forms of nitrogen) and add to the oxygen demand of the wastewater. Methods and procedures will be presented along with the importance of testing BOD/CBOD in the wastewater treatment facility.

CHED 161

Refractive index of malonic acid measured by Zoom-In method

Brian Um, [email protected], Jun H. Shin. Department of Chemistry, Queensborough Community College, CUNY, Oakland Gardens, New York, United States

Recently we have developed a method for determining the refractive index of solid compounds: the zoom-in method. The zoom-in method was based on the observation that the refractive index of a liquid remains unchanged with the addition of a solid if the refractive index of the solid is the same as the liquid. To choose two qualified solvents, a preliminary test was conducted using 3-8 different solvents: one showed an increase and the other underwent a decrease in the refractive index with the addition of malonic acid. Solutions of varying concentration (% mass) were prepared with the two solvents selected, and the refractive index of each prepared solution was measured. The value was compared to the refractive index of the same solution with malonic aicd dissolved in it (10% mass) until two values were matched. The matched value was the refractive index of malonic acid. The refractive index of malonic acid has been determined by the zoom-in method by three sets of solvent systems: DMSO/THF, BzOH/THF, and BzOH/n-PrOH. In BzOH and THF solvent system, the refractive index of malonic acid was found to be the same as a 41% BzOH solution in THF, having a refractive index of 1.461(1). The same procedures were repeated with two other solvent systems, and the refractive index was measured as 1.458(1) and 1.455(1) which were close to the result obtained from BzOH/THF system. The zoom-in method turned out to be a useful system in measuring the refractive index of solid compounds.

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CHED 162

Determination of the refractive index of benzoic acid measured by Extension method

Ha Eun Kim, [email protected], Jun H. Shin. Department of Chemistry, Queensborough Community College, CUNY, Oakland Gardens, New York, United States

The extension method which was developed based on the observation of a good linear relationship between the percent mass of solution (solid solute and liquid solvent mixture) and its refractive index has been used to determine the refractive index of solid compounds such as fatty acids and ionic compounds. In the system, a plot of refractive index vs percent mass was obtained in low concentration ranges (0 - 24%), and the line of the linear plot was then extrapolated to 100% mass (i.e. pure solid) where the refractive index of the solid was calculated. The extension method has been further applied to measure the refractive index of benzoic acid because it showed good solubility in various organic solvents such as DMSO, ethanol, methanol, and THF. In the experiment, a linear plot was obtained between the refractive index and % mass of benzoic acid in a solvent, and a first order linear equation was calculated based on the plot. By applying 100 to the % mass variable (100% mass means pure solute, the solid compound) in the linear equation, the refractive index of benzoic acid was indirectly determined for the solvent. Based on the data measured in DMSO solution of benzoic acid, a linear equation (e.g. y=0.000690x + 1.476774) was obtained, then a value of 100% was applied to get the refractive index of benzoic acid, which was 1.546. After two more trials, 1.546(1) was determined as the refractive index of benzoic acid in DMSO.

CHED 163

Thermodynamic study of esterification using a microwave reactor

Hyeon Yun1, [email protected], Eun Jung Shin2, Jun H. Shin1. (1) Department of Chemistry, Queensborough Community College, CUNY, Oakland Gardens, New York, United States (2) Queens College, CUNY, Flushing, New York, United States

Microwave reactor is a new technology and has become an invaluable tool adopted in many areas of science laboratories due to the convenience including temperature, pressure and power controls. Application of a microwave reactor was further extended to the thermodynamic study of esterification reaction with the merit of a convenient temperature control of a microwave reactor. The equilibrium constants of the esterification reaction between acetic acid and isopropanol at the temperatures of 50 - 90°C were determined from the initial and equilibrium concentrations of acetic acid through the acid-base titration using a 0.5M NaOH solution. Thereafter, the thermodynamic data (ΔH and ΔS) of the reaction were calculated from the linear relationship between the equilibrium constants obtained (lnK)

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and the equilibrium temperatures (1/T). Similarly, the thermodynamic data of the esterification reaction between acetic acid and n-propanol were also obtained using a microwave reactor. The obtained data were compared to the data calculated from the acetic acid/isopropanol reaction. This result will extend the usage of microwave reactor to a tool of the thermodynamic study which can be easily added to an undergraduate laboratory curriculum. Application of a microwave reactor will make the thermodynamic study easy, simple and faster due to the convenience of the temperature control of the instrument and its safety features.

CHED 164

Determination of the ionization constant of weak carboxylic acids using microscale freezing point depression measurements

David Kwun, [email protected], Pedro Irigoyen, Paris D. Svoronos. Chemistry, Queensborough Community College, Bayside, New York, United States

Freezing point depression is a colligative property that is related only to the number of particles in solution but not to the nature of the solute. For the first time the ionization constant of a carboxylic acid is determined in a non-traditional titrimetric method. The values obtained are also the first ones ever recorded at 0oC. The project uses microscale freezing point depression measurements to calculate this physical property using the Van’t Hoff factor. The investigation involves the study of several carboxylic acids(Ka=10-2 – 10-3) . The ionized fraction of the solute is measured through a derived equation that correlates the freezing point depression temperature. The measured Ka values of various carboxylic acids were determined at various aqueous concentrations (1.00M, 0.50M, 0.25M, 0.10M). The experiment is fast, uses extremely low concentrations of the solute and the results are easily reproducible.

CHED 165

Study of Donnan equilibrium and specific ion effect on osmometry measurements in urine

Caroline Furrh, [email protected], Randol Vick, Michele S. McAfee. Medical Lab Science, Tarleton State University, Fort Worth, Texas, United States

Maintenance of adequate body fluid volume and correct distribution of this fluid between the body compartments is a critical component of homeostasis. The kidney plays an essential role in this homeostasis; therefore, urinalysis is an excellent indicator of fluid balance. The most common method for evaluating urine in the laboratory is osmometry. However, urine is a very complex biological fluid containing a variety of substances, such as urea, proteins, salt and glucose. To study their effects and interactions on osmometry measurements, a series of artificial urines were prepared containing known concentrations of glucose, albumin, and several different salts (NaCl, KCl, CaCl2,

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NH4Cl, MgCl2, MgSO4, Na2SO4, K2SO4 and (NH4)2SO4) and analyzed using this technique.

CHED 166

Determination of positive results in colorimetric presumptive drug tests by ultraviolet spectrometry

Ryker Kern, [email protected], Gregory P. Foy. York College of Pennsylvania, Oxford, New Jersey, United States

Forensic drug identification requires a series of tests to determine if a substance is an illicit drug. Identification begins with presumptive tests which are used to narrow down the possibilities. This research is focused on colorimetric tests (presumptive), in which a reaction occurs between a target functional group and the reagent causing the solution to change to a known color indicating a positive reaction. The first part of this project is to determine if there is a reliable correlation between the color intensity and the purity of the illicit drug. The second part of the project is a creation of a standardized method to determine the most intense wavelength corresponding to the absorbance. This will eliminate the debate of color perception, especially in court. Qualitative and quantitative analysis will be performed using ultraviolet-visible spectroscopy (UV-Vis). Field kits can be created to include inexpensive handheld UV-Vis and colorimetric tests for use as presumptive field tests.

CHED 167

Manipulating signal hydrophobicity to alter quorum sensing in Streptococcus pneumoniae

Erin Tiwold, [email protected], Michael A. Bertucci. Chemistry, Moravian College, Bethlehem, Pennsylvania, United States

The bacterial species Streptococcus pneumoniae utilizes a process known as quorum sensing to communicate with each other and coordinate group gene expression based on the number of neighboring cells. During quorum sensing, bacteria produce a signaling molecule that is released outside the organism and at a certain concentration can initiate group gene expression for host infection. Thus, inhibiting the quorum sensing mechanism is a unique anti-infection strategy that will not wipe out the bacteria population but create an environment where the bacteria believe they are present at low density and will not initiate virulence mechanisms. S.pneumoniae was an ideal bacteria to study since the signaling molecule (a peptide known as CSP1) has already been identified. We employed synthetic organic chemistry to make a library of CSP1 derivatives, focusing on modification at a uniquely hydrophobic region of the peptide that was hypothesized to be critical for receptor binding and initiating gene expression. Using the purified and identified CSP1 derivatives we will determine experimentally the anti-quorom sensing and anti-biofilm formation activity of the bacteria by screening in

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live S.pneumoniae cultures. These derivatives will not only allow us to study how the peptide binds to the receptor, but may also serve as inhibitors of the native peptide, CSP1. This would decrease the efficiency of the bacteria to communicate with one another and attenuate virulence.

CHED 168

Purification and characterization of two probable lipases implicated in the virulence of Mycobacterium tuberculosis

Daniel Schemenauer, [email protected], Randal Johnson. Chemistry, Butler University, Indianapolis, Indiana, United States

Tuberculosis (TB) remains one of the most prevalent diseases in the world, infecting one third of the world’s population. The causative agent, Mycobacterium tuberculosis, relies on a plethora of lipid degrading enzymes known as lipases to maintain an infection in its host. With such a large portion of its genome dedicated to lipid metabolism, lipases have become a viable target for drug development, especially as targets for the dormant state of M. tuberculosis. An array (94) of gene products of this bacterium have been identified as having the α/β hydrolase fold with 24 genes of the Lip family being characterized as possible lipases/esterases. Many of these Lip family gene products are however poorly characterized, preventing further inhibitory drug designs. The aim of this study was to characterize the thermal stability and enzymatic activity of two enzymes of the Lip gene family (LipM and LipO). Proteins were expressed and purified using nickel affinity chromatography. Melting point (Tm) measurements were made using differential scanning flourimetry and enzymatic kinetics were measured through hydrolysis of a fluorogenic hydrolase substrates. Thermal stability was determined to be near identical, whereas differential enzymatic activity was observed for the two probable lipases. Future studies will aim to determine the substrate specificity of both LipM and LipO.

CHED 169

Identification of M. tuberculosis enzymes expressed under dormant growth conditions

Brent S. Waibel, [email protected], Randal Johnson. Chemistry, Butler University, Indianapolis, Indiana, United States

Mycobacterium tuberculosis is responsible for the most deaths of any one single infectious agent in the world. This research investigated the transition of M. tuberculosis between its active and dormant state and the enzymes required to complete this transition. The main target of this research was to identify enzymes (lipases and esterases) used by M. tuberculosis for energy production in the dormant state. This was accomplished by first inducing dormant conditions to M. smegmatis, a nontoxic relative of M. tuberculosis. Next, the total enzymes from M. smegmatis were isolated and

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separated based on their size and charge using Native-PAGE gel electrophoresis. Once the enzymes were separated, the esterase and lipase enzymes were isolated by using a fluorescent sensor that only activated in the presence of these two classes of enzymes. The relative amounts of these enzymes between normal and dormant growth conditions were then examined and compared by their relative sensor intensity on the gel. Finally, the identification of the enzymes that were activated under dormant conditions was accomplished by cutting the segments out of the gel and analyzing them by mass spectrometry. This research has long-term implications in the identification of novel drug targets for dormant M. tuberculosis infections.

CHED 170

Determining the thickness of droplet interface bilayers from capacitance measurements using a modified electrophysiological amplification technique

Mick E. McGlone, [email protected], Sunghee Lee. Chemistry, Iona College, New Rochelle, New York, United States

The cell membrane has many properties crucial to the life of the cell, one of which is to act as a semi-permeable barrier to determine the molecules that can pass through it. The main way this selectivity is regulated is through the use of trans-membrane transport proteins. Due to the specificity of these proteins and their sizes and shapes, the membrane that they span must be of a particular thickness. Membrane thickness is predominantly determined by the types of lipids that make up the membrane, particularly the chain length and bond structure of the hydrocarbon chain. In this project, a highly efficient method for determining the thickness of membranes has been developed using the Droplet Interface Bilayers (DIB) as a model system for the cell membrane. This method measures the capacitance of the membrane and thus determines membrane thickness owing to the inverse relationship between capacitance and membrane thickness. These studies can be used to highlight the ways in which membrane thickness can be modulated and thus tune the activity of transport proteins.

CHED 171

Influence of intercalant on the lipid bilayer membrane: Water permeability studies

Gabriella Di Domizio, [email protected], Maria Lopez, Jake Villanova, Peter Milianta, Jacqueline Denver, Sunghee Lee. Chemistry, Iona College, New Rochelle, New York, United States

The ability to understand membrane permeation is of critical importance, as the transport of small molecules across bilayer membranes has significant implications for cellular physiology and homeostasis. Among molecules transported by passive permeations, the permeability of water molecules across cellular membranes has been widely investigated in order to understand how the rate of water flow is controlled as a function of lipid bilayer composition, structure and property in various cellular

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membranes. In this study, using a droplet interface bilayer as a membrane model, we determined water permeability of the membrane. The DIB is a simple technique for constructing a stable lipid bilayer at the interface of two water droplets submerged in oil containing bilayer forming lipid. To achieve better understanding of the properties of DIB, we have studied the effect of nonpolar oil and other intercalants that can potentially influence the characteristics of the DIB, in terms of water permeability of the membrane. Our methods in quantifying physical properties of membranes will provide direct insight into how their structures impact their functions.

CHED 172

Effects of cis and trans double bonds on lipid membrane properties

Jacqueline Denver, [email protected], Alessandra M. Armetta, Sunghee Lee. Chemistry, Iona College, New Rochelle, New York, United States

Biological membranes consist of lipids not only of saturated hydrocarbon chains but a large fraction of hydrocarbon chains having at least one unsaturation which can have cis and/or trans isomers in their hydrocarbon chain. Lipids containing trans double bonds closely mimic the properties of saturated fatty acids. Trans lipids have been shown to appear increasingly in the body with diet due to the processes of hydrogenation in order to increase shelf life of packaged foods. Increased concentrations of trans lipids in the biological membrane have shown to contribute to abnormal physiological developments including coronary artery disease and arteriosclerosis. The double bond arrangement, either cis or trans, in the hydrocarbon chain of the lipid can have profound effects on the membrane properties. In this study, we report our systematic study on the effect of acyl chain double bonds between cis and trans-forms on energetics of water permeability. We studied unsaturated monoacylglycerols and phospholipid membranes with a hydrocarbon chain consisting of 16 and 18 carbon atoms. Our findings will add to the current understanding of the difference in conformational disorder between cis and trans forms of unsaturated hydrocarbon chain of lipid.

CHED 173

Biomimetic membrane and ion effects: Water permeability and thermal property

Sue Ellen Evangelista, [email protected], Jacqueline C. Martinez, Melissa E. Morales, Sunghee Lee, [email protected]. Chemistry, Iona College, New Rochelle, New York, United States

The plasma membrane is a complex amalgam of proteins, lipids and carbohydrates that work together to perform various tasks such as the provision of structure and regulation of transport into and out of the cell, particularly water transport. Ions have significant effects on the properties of these semi-permeable membranes due to their abilities to bind to the phospholipid bilayer and alter its structure. Therefore, it is expected that the

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interaction of ions and lipids in a bilayer should be manifested in the permeability of species across the bilayer. Using the Droplet Interface Bilayer System (DIBS), we have investigated the effect of various cations and anions on the water permeability and thermal properties of lipids membranes. Lipids we used differs in nature and charge of the headgroup, e.g., monoglycerides having no charge, zwitterionic phosphatidylcholine, and anionic phosphatidylserine. Additionally, lipids were varied in tail structure having different degree of unsaturation. Our findings from this study allows us to probe the extent in which ions interact with the particular lipid component of a bilayer.

CHED 174

Mitigating condensation by cholesterol with unsaturated lipids: Effect on permeability

Maria Lopez, [email protected], Gabriella Di Domizio, Sue Ellen Evangelista, Melissa E. Morales, Sunghee Lee. Chemistry, Iona College, New Rochelle, New York, United States

Free-standing membranes are used as models for drug delivery devices and artificial cell membranes. Droplet Interface Bilayer (DIB) can be employed as a convenient free-standing model membrane to explore structural effects on bilayer water permeability. Cholesterol is present in mammalian cellular membranes as a high fraction of total lipid

(∼20−50 mol %), and plays a crucial role, principally in its organizing effect upon other lipidic components of the membrane. Model membranes have been widely used to explore the molecular consequences of the presence of cholesterol in biomembranes. In this study, we have measured osmotic water permeabilities and activation energy for water permeation of an associated series of monoglycerides and phospholipids as the principal component of droplet bilayers in the presence of a varying concentration of cholesterol. Our finding suggest that the effect of cholesterol on the water permeation process differs depending on the tailgroup structure in a series of monoglycerides bilayers.

CHED 175

Immobilization of light-driven P450 biocatalysts as cross-linked enzyme aggregates

Evelynn Henry, [email protected], Mallory Kato, Lionel E. Cheruzel. Chemistry, San Jose State University, San Jose, California, United States

A lack of long-term operational stability coupled with difficulty in recovering and re-using soluble enzymes has often limited their industrial applications. However, immobilization has been shown to enhance enzyme stability under both storage and operational conditions, minimizing denaturation by heat or organic solvents. Cross-linked enzyme aggregate (CLEA) technology offers many advantages over other means of

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immobilization, including simplicity and rapid optimization. CLEAs have found wide applications in immobilizing various enzymes including hydrolases, lipases and a few oxidoreductases. In terms of synthetic capability and industrial applications, cytochrome P450 enzymes are of particular interest, as they are capable of performing a variety of selective oxidation reactions on unactivated C-H bonds. Our laboratory has recently developed light-driven P450 biocatalysts that display high photocatalytic activity and initial reaction rates in the hydroxylation of a wide range of substrates. In pursuit of our interest in utilizing P450 BM3 for biotechnological applications, we have investigated the cross-linking of P450 BM3 enzymes. We have thus explored several cross-linking conditions using a colorimetric assay for the CLEA optimization process. We will present our latest findings regarding the optimization of the CLEAs and their activity for several rounds of reactions upon light activation.

CHED 176

Establishing preliminary relationships between peptide structure and quorum sensing activity in Bacillus cereus

Jessica K. Lynch, [email protected], Michael A. Bertucci. Chemistry, Moravian College, Bethlehem, Pennsylvania, United States

Bacterial quorum sensing is a chemical communication process that plays a role in biofilm growth and bacterial virulence. Understanding this process has practical applications in creating new therapeutics that silence this communication circuit, and can hopefully help in solving some of the problems pertaining to the resistance of bacteria to current antibiotics. Our project will modify the autoinducer that signals biofilm growth in Bacillus cereus, mild opporunistic pathogen. This autoinducer is a peptide sequence of seven amino acids that binds to a receptor in the bacterial cell. In our study, we have synthesized seven different peptides via alanine scanning to see which amino acids are most important in receptor binding and initiation of the quorum sensing mechanism. Ultimately, we would like to test the peptides we synthesized in a bacterial assay to see if they successfully inhibit quorum sensing and biofilm production.

CHED 177

Inhibition of cancer cell viability using lysyl oxidase inhibitors

Kathryn A. Johnston, [email protected], Karlo M. Lopez. Chemistry and Biochemistry, California State University, Bakersfield, Bakersfield, California, United States

Lysyl oxidase (LOX) is a copper-dependent amine oxidase that has been implicated in playing a paradoxial role in cancer. Expression of the LOX gene was found to inhibit the transforming activity of the H-ras oncogene in NIH 3T3 fibroblasts. Ras proteins are involved in transmitting signals within cells and are the most common oncogene in human cancers. It was hypothesized that the activity of LOX can be controlled through

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the use of mechanism-based inhibitors in MDA-MB-231 breast cancer cells. Selective inhibitors for lysyl oxidase were synthesized and assayed for cell viability using breast cancer cells. The inhibitors synthesized were the meta and para derivatives of 4-nitrobenzyl β-APN, the para derivative of 4-bromobenzyl β-APN, and the dibenzyl derivative of β-APN. A three-day viability assay following the treatment of cancer cells with these derivatives revealed that cells treated with the meta derivative of 4-nitrobenzyl β-APN, the para derivative of 4-bromobenzyl β-APN, and the dibenzyl derivative of β-APN had a significant decrease in cell viability when concentrations greater than 500 μM were used. The para derivative of 4-nitrobenzyl β-APN, however, had little effect on the viability on the cells. These results indicate that the meta derivative of 4-nitrobenzyl β-APN, the para derivative of 4-bromobenzyl β-APN, and the dibenzyl derivative of β-APN are successfully targeting the cancer cells, although it remains to be seen whether or not the inhibitor is selectively targeting lysyl oxidase. Normal breast cells are currently being tested in order to ensure that the inhibitory effect is only present in cancer cells.

CHED 178

Enzymatic regulation of the extracellular matrix

Igor Gojkovic, [email protected], Laurie Grove. Sciences, Wentworth Institute of Technology, Boston, Massachusetts, United States

The body has many natural systems that control the homeostatic conditions of the local environment. Our research delves into tissue remodeling, specifically, the enzymes that regulate the extracellular matrix (ECM), with special focus on matrix metalloproteinases (MMPs), which are enzymes that break specific peptide bonds of ECM proteins. MMP activity was explored in the context of two different applications: (1) activity in cancerous cells, and (2) repair of scar tissue. Exploratory studies into the enzyme kinetics of MMP-2 were conducted using absorption spectroscopy and fluorescence resonance energy transfer (FRET) at varying pH levels to simulate normal and cancerous conditions within the body. Initial findings showed greater activity within cancerous acidic conditions (pH 6.4). Additional studies on kinetic data for each substrate will be compared to determine how the reaction rate of the enzyme changes in various conditions. Current experiments include enzyme kinetics of MMP-1 and collagen I, a major component within the ECM. Insolubility of collagen I has proven to be problematic for testing; however, with heat and centrifugation the protein was forced into solution. SDS-PAGE will be used to determine the products of the reaction along with kinetic data. Collagen I has been chosen due to its presence throughout the body as well as its role in scar tissue buildup. Controlling the buildup of scar tissue within damaged tissue is an area of interest due to the detrimental effects scar tissue poses on full tissue regrowth. The basis of this study and future studies is to be able to control the production and destruction of the ECM to be able to direct tissue remodeling in situ.

CHED 179

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Characterizing the pH responsiveness of dithiolane-modified peptide self-assembly structures

Ruben Neves, [email protected], Jillian E. Smith-Carpenter. Chemistry and Biochemistry, Fairfield University, Fairfield, Connecticut, United States

Recently, there has been great effort to develop a set of “bottom-up” design strategies that direct the assembly of peptides into specific supramolecular structures. The factors that control and stabilize peptide self-assembled structures, including side chain electrostatic interactions, sterics, and hydrophobicity, are non-covalent, and therefore reversible. One strategy to expand and diversify the intermolecular stabilizing interactions of peptide self-assembly involves the integration of dynamic covalent disulfide chemistry. Herein, we report the synthesis of lipoic acid-modified peptides and the characterization of the dynamic disulfide network on the supramolecular structures. The responsiveness of the supramolecular peptide surface disulfide-exchange polymerization to pH changes was investigated spectroscopically. The combination of dynamic covalent disulfide chemistry and peptide self-assembly will expand the current chemical diversity of biomaterials to yield environmentally responsive supramolecular assemblies with reactive surfaces.

CHED 180

Dissociation constant measurements of fluoride binding in heme proteins and the effects of the distal amino acid

Kaleigh Williams1, [email protected], Kaitlyn Frankenfield1, [email protected], Darya Rivera2, Juan Lopez Garriga2, Jose Cerda1. (1) Chemistry, Saint Joseph's University, Philadelphia, Pennsylvania, United States (2) Chemistry, University of Puerto Rico-Mayaguez, Mayaguez, Puerto Rico, United States

Dissociation constants (Kd) for fluoride binding were measured as a function of pH for hemoglobin (Hb), myoglobin (Mb), horseradish peroxidase (HRP), and hemoglobin I from L. pectinata (HbI) from pH 4.5 to 8.5. Our study shows that the affinity for fluoride is strongest at low pH for all the studied heme proteins. However, of the four, HRP has the strongest affinity for fluoride with a Kd value of 0.001 M. Past studies have shown that stabilization to the heme-bound fluoride ion is achieved via electrostatic interaction between the fluoride and the positively charged distal arginine residue. On the other hand, of the four studied heme proteins, HbI has the lowest affinity for fluoride with a Kd value of 0.07 M at pH 5. This affinity is 7 times lower than that of Hb and 20 times lower than Mb at the same pH. Hb and Mb both have a protonated distal histidine residue at pH 5, which stabilizes the heme-bound fluoride ion via H-bonding. The low affinity of fluoride binding in HbI indicates that its heme pocket is designed to minimize H-bonding towards the anionic ligand. The results of this study indicate the utility of fluoride ion as a probe of heme pocket-protein interactions.

CHED 181

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Conserved heme domain residues play an important role in the oxygen sensing mechanism of the heme-PAS and histidine kinase FixL protein from S. meliloti

Mark Reynolds, Joseph Collins, Paul Gronski, John Paul Hagerty, [email protected], Jennifer Schadt. Chemistry and Biochemistry, Saint Joseph's University, Philadelphia, Pennsylvania, United States

The oxygen sensing FixL protein from Sinorhizobium meliloti regulates nitrogen fixation and microaerobic respiration and is part of the heme-PAS and histidine kinase family of sensors. Site-directed mutagenesis was used to study the role of several conserved residues in the heme domain of SmFixL. The conserved residues Y197A and R200 were found to play important roles in oxygen binding and may play an important role in signal transduction. Spectroscopic studies with UV-Vis, resonance Raman and CD spectroscopy reveal the importance of these amino acids in oxygen binding. An understanding of the oxygen sensing mechanism of FixL can be applied to other proteins in this family. Kinase assays of these site-directed SmFixL* mutants are ongoing.

CHED 182

Evaluation of recombinant Hsp70α mutants for heat shock protein binding and chaperone activity

Austin Lieber, [email protected], Cuong V. Nguyen, [email protected], Rebecca E. Connor. Chemistry, Dickinson College, Carlisle, Pennsylvania, United States

The exposure of cells to electrophilic compounds is a common event with exposures ranging from endogenously derived reactive species to environmental or therapeutic molecules. Two residues within human Hsp70α, Lys597 and Cys603 were identified as potential sites for modification by therapeutic electrophiles such as parthenolide. In order to investigate the effect of electrophilic modification on Hsp70 function, we have designed a series of mutants that cannot be modified by electrophiles. Lys597 was mutated to alanine and glutamine. Each of six cysteine residues found in Hsp70α were mutated to both serine and alanine. The resulting mutant proteins were evaluated for binding to Hsp40 and Hsp90 using biolayer interferometry both with and without the presence of electrophilic compounds. The chaperone activity of the Hsp70 mutants was also determined using model proteins, firefly luciferase and β-galactosidase.

CHED 183

Assessing the fluoro-stabilization effect using in vivo unnatural amino acid incorporation

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Dominic Parfianowicz, [email protected], Alexander Miner, [email protected], Christopher Henkels. Chemistry, Wilkes University, Wilkes-Barre, Pennsylvania, United States

The substitution of fluorinated analogs of amino acids into proteins may prove a useful strategy in protein design given fluorine’s unique chemical properties, minimal structural perturbation and enhanced polypeptide stability upon incorporation. Understanding the magnitude, thermodynamic and mechanistic basis of the “fluoro-stabilization effect” is currently an active field of research. While incorporation of fluorous amino acids have yielded an increase in protein stability against both temperature and denaturants in most studies, several factors preclude a consensus estimate for the enhanced stability of a fluorocarbon bond substitution for a hydrocarbon bond. Furthermore, most studies have examined small fluorinated polypeptides (< 60 residues), which may amplify any thermodynamic effect upon mutagenesis. Here, we have developed a systematic study to examine the magnitude and molecular basis of fluoro-stabilization using an array of in vivo translated fluorine-unnatural-amino-acid-(F-UAA)-containing single-site superfolder green fluorescent protein (sfGFP) variants. Overall, we incorporated four (predominantly) F-UAAs at the two external positions, totaling eight sfGFP vairants. Interestingly, denaturant equilibrium unfolding experiments suggest that fluorocarbon bond substitution destabilizes sfGFP in a position-dependent manner. This atypical result may have intriguing implications for the denatured state of fluorinated sfGFP variants, as spectroscopic data suggest that F-UAA substitution at either solvent-exposed substitution site does not affect native sfGFP secondary or tertiary structure.

CHED 184

Investigating the determinants of structure, stability, and folding in a model protein system: GB1

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Brittney Ruedlinger, [email protected], John Bedford, Lesley H. Greene. Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia, United States

The β1 domain of Streptoccocal protein G (GB1) is under investigation as we search to further understand how sequence directs the three-dimensional nature of protein folding and stability. GB1 exemplifies a two-layer alpha-beta sandwich and consists of 56 amino acids (Figure 1). Experimental and computational studies were implemented to explore pivotal interactions among residues. Our results will be presented.

Figure 1. The native structure of GB1. The image was visualized using RasMol (PDB code:

1pgb). β-strands are depicted in yellow and the α-helix in pink.

CHED 185

Bacterial growth studies of gut microbes including Lactobacillus Rhamnosus GG and Escherichia Coli HS using UV-VIS spectrophotometry and quantitative PCR (QPCR)

Devashri Parikh, [email protected], Seung-Sup Kim, Pritha Aggarwal, Katerina Djambazova, [email protected]. School of Theoretical and Applied Science, Ramapo College of New Jersey, Mahwah, New Jersey, United States

The long term goal of this project is to understand the symbiosis among gut microbes and the current goal of the project is to develop a quantitative analysis method to

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measure the growth of specific gut microbes including Escherichia coli HS and Lactobacillus Rhamnosus GG in cell mass or at an RNA level. This work reports on the early stage of the growth study of the target bacteria using UV-VIS spectrophotometry and quantitative PCR analysis. The specific strains of the two target bacteria in use have been identified using common 16S rRNA sequencing. The growth studies of both bacteria were completed under aerobic and anaerobic conditions. For the UV-VIS spectrophotometry analysis, an OD600 measurement was used and the result clearly showed the differences in the growth phases of the two different bacterial strains under the same growth conditions (tryptic soy broth media, 37 °C and aerobic or anaerobic). For the QPCR analysis, a 16S rRNA template was employed and the results showed similar outcomes with the growth studies using the UV-VIS spectrophotometry for E.coli HS. Currently, we are trying to connect the two different quantitative bacterial growth analysis techniques including cell mass analysis using UV-VIS spectrophotometry and quantification of 16S rRNA using quantitative PCR. In the future, this combination of the two different methods may provide us one of the possible tools to quantitate a specific bacterial strain from a mixture of different microbes using strain-specific PCR primers.

CHED 186

Effect of metals on catalytic activity of mutated Rv0045c esterase from M. tuberculosis

Isobel Bowles, [email protected], Ben Lancaster, Randal Johnson, Geoffrey C. Hoops. Chemistry, Butler University, Indianapolis, Indiana, United States

The goal of this experiment was to identify the allosteric binding site of +2 metal cations on the Rv0045c protein, an esterase of M. tuberculosis, leading to better understanding of its regulation. To accomplish this goal, two amino acids aspartate (D314) and histidine (H223) proposed to be possible allosteric binding sites of +2 metal cations in the Rv0045c protein were studied for the effect on the metal dependent catalytic activity of Rv0045c. Using a specific DNA primer, those two amino acids were mutated to alanine, resulting in mutant Rv0045c plasmid DNA (D314A and H223A). The mutant Rv0045c plasmid was transformed into E. coli, and the protein was expressed at high concentrations, and then purified to homogeneity using Ni-metal affinity chromatography. The presence, purity, concentration, and stability of the Rv0045c variants were then confirmed by SDS-PAGE, absorption spectroscopy, and differential scanning fluorimetry. Analysis of the kcat/KM ratio from steady state initial rate data, comparing original Rv0045c to its mutants, determined the relative catalytic activity of the mutants, to give a better understanding of how 2+ metal cations affect the Rv0045c protein.

CHED 187

Characterization of a triacylglycerol lipase from Mycobacterium tuberculosis

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Jakob Jozwiakowski, [email protected], Randal Johnson. Chemistry, Butler University, Indianapolis, Indiana, United States

The pathogen Mycobacterium tuberculosis is able to enter a state of dormancy in which the central metabolism shuts down. In this state, the pathogen is resistant to drug treatment and difficult to identify in host organisms. The triacylglycerol hydrolase LipY is a potentially key lipid metabolism enzyme controlling this dormant state transition from Mycobacterium tuberculosis. Herein, we cloned the LipY protein, expressed the protein in E. coli, and characterized the detailed substrate specificity of LipY. Initially, the LipY gene was cloned from the H37Rv Gateway cloning library into an expression vector and a C-terminal stop codon was successfully added by Quikchange mutagenesis. Optimal conditions for LipY expression were then determined using a range of E. coli expression strains and variable protein expression conditions (time, temperature, and induction agent). Active LipY protein was then isolated by Nickel-affinity chromatography and confirmed by SDS-PAGE. Thermal stability reinforced that LipY was fully folded and stable at room temperature. Detailed substrate specificity measurements illustrated the diverse substrate reactivity of LipY, but reaffirmed the preference for longer chain substituents. The final substrate specificity profile for LipY can now be compared to other mycobacterial hydrolases to determine the unique chemical reactivity of LipY.

CHED 188

Using directed evolution to increase lipid formation in Chlorella vulgaris for use in biofuels

Amanda Smythers, [email protected], Paris E. Adkins, Aaron Holland, Derrick Kolling. Chemistry, Marshall University , Huntington, West Virginia, United States

Microalgae, with their ability to grow in adverse environments using a variety of water sources, is an advantageous source of energy that will not compete with food supply and can potentially assist in the treatment of wastewaters. Chlorella vulgaris has been previously shown to be a high lipid producing microalgae with an average 42 percent dry weight lipid content under nitrogen deprivation. This experiment aims to increase the accumulation of lipids in C. vulgaris through applied natural selection, or directed evolution, to create a modified C. vulgaris culture with increased acetyl-CoA carboxylase (ACCase) activity. A less expensive method of genetic engineering, applied natural selection can theoretically be repeated without the constraint of restrictive technology, potentially enabling microalgae users to undergo the process to increase the productivity of industrial microalgae cultures. ACCase is the starting point of the lipid synthesis pathway and cannot be bypassed in the production of triglycerides. Research at the American History Museum demonstrated that one may use sethoxydim, a member of the cyclohexanedion family of herbicides, to induce the overexpression of ACCase in Nannochloropsis salina, resulting in a sevenfold increase in lipid content. We aim to expand upon that research by measuring the effect of sethoxydim on C. vulgaris and comparing it to the effect of an aryloxyphenoxypropionate herbicide, a fellow

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ACCase inhibitor. To-date, our results have shown moderate success in increasing lipid production.

CHED 189

Building a library of fluorogenic ester substrates to analyze serine hydrolases

Andrew Koelper, [email protected], Randal Johnson, Geoffrey C. Hoops. Chemistry, Butler University, Indianapolis, Indiana, United States

Mycobacterium tuberculosis, the organism responsible for the respiratory infection tuberculosis, has evolved multi-drug resistance strains, introducing the need for novel drug targets. Various esterases have been sought as targets to surpass multi-drug resistance. Inhibition of these esterases could terminate the bacterial cell and resolve tuberculosis infection. Competitive inhibition requires a close mimic to the natural substrate of these enzymes. The identity of these esterases has been determined using DNA genomic screening, but evidence for the natural substrate is still unknown. A library of fluorogenic ester derivatives has been created to screen against various esterases. Previous work has compiled a library of bis-substituted fluorescein ester derivatives; however, mono-substituted ester derivatives, containing two different R chains, had not been synthetized. Substrates containing two distinct R chains allow further experimentation of substrate specificity. In addition, the library had been limited to a single heteroatom in each derivative, but was expanded to contain multiple heteroatoms within each derivative. Introduction of additional electronegative atoms and polar bonds allows for additional opportunities for catalytic binding and substrate specificity. Synthesis of novel compounds required separation techniques including silica-gel column chromatography, along with characterization techniques including 1HNMR and 13CNMR and high-resolution mass spectroscopy.

CHED 190

Biophysical characterization and catalytic reactivity of rubrerythrin and symerythrin model proteins

Jenna Pellegrino1, [email protected], Katherine A. Bell1, Rachel Polinski1, Sabrina Cimerol1, Ari Jacobs2, Edward I. Solomon2, Amanda J. Reig1. (1) Chemistry, Ursinus Colelge, Phoenixville, Pennsylvania, United States (2) Chemistry, Stanford University, Stanford, California, United States

The ferritin-like superfamily (FLSF) is a class of 4-helix bundle proteins that contain a diiron active site and participate in important biochemical pathways, including fatty-acid desaturation and the formation of deoxyribonucleotides. The canonical FLSF metallocenter is ligated by four carboxylate and two histidine residues. However, rubrerythrins (Rbr) and symerythrins (Sym) display one and two additional active site carboxylate residues, respectively. These proteins exhibit enhanced reactivity with hydrogen peroxide relative to other members of the FLSF, but the correlation between

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the additional carboxylate residues and the altered functionality is currently not well understood. We have created models of Rbr and Sym based on G4DFsc, a small, de novo-designed 4-helix bundle protein that mimics the canonical structure and reactivity of FLSF enzymes. Aspartate (D) or glutamate (E) residues were introduced at positions G14, G43, and/or G47 to generate Rbr- and Sym-like active sites within the G4DFsc bundle. The structural and catalytic properties of these systems were investigated using metal-binding, protein-folding, and reactivity assays at pH 7 and pH 7.5. Data show that the double mutants exhibit the weakest metal-binding capacity at pH 7. Yet, these proteins also show greater rates of 4-aminophenol oxidation than the original G4DFsc protein. The G47D variant shows the greatest catalytic capacity, increasing rates of 4-aminophenol oxidation by over eight times compared to G4DFsc. These results provide insight into how particular carboxylate residues in the G4DFsc active site affect its ability to react with dioxygen and hydrogen peroxide.

CHED 191

Synthesis and characterization of self-assembling nucleopeptides

Kimberly DelBianco, [email protected], Samantha R. Schrecke, [email protected], Samantha Brown, [email protected], Jillian E. Smith-Carpenter. Chemistry and Biochemistry, Fairfield University, Fairfield, Connecticut, United States

In the complex environment of cells, biomolecular structures have evolved a delicate balance between stability and dynamic responsiveness. Both of these factors rely on the strength and diversity of non-covalent interactions. In an effort design more responsive biomaterials, we have integrated the recognition elements of nucleic acids with self-assembling peptides. Herein, we report the synthesis of guanosine modified short peptides (nucleopeptides) and the characterization of the resulting supramolecular structures assembled in various conditions. Infrared spectroscopy (IR) was used to identify the major secondary structures, G-quartets and extended β-sheet formations, while Atomic Force Microscopy (AFM) was used to image the supramolecular fibers that form. Information from these self-assembling nucleopeptide studies willextend current strategies for “bottom-up” control of final morphology.

CHED 192

Antiphospholipid antibody and MiR106b mediated expression of tissue factor in breast cancer cell lines

Irene Sun1, [email protected], Elaine Lin2, Regina Sullivan1, Andrew Nguyen1. (1) Biological Sciences and Geology, Queensborough Community College, Bayside, New York, United States (2) Cell, Developmental & Cancer Biology, , Oregon Health & Science University, Portland, Oregon, United States

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A link between coagulation and clinical outcome of patients with cancer has been well established. Tissue factor (TF), a transmembrane glycoprotein known originally as the initiator of blood coagulation cascade, has recently been demonstrated to modify cancer microenvironment and angiogenesis. We have recently shown that anti-phospholipid antibody (aPL) mediate breast cancer tumor progression in xenograft model by up regulation of TF. We have further demonstrated that aPL stimulates TF expression in less aggressive tumor cell line (MDA-MB-468) but not aggressive cell line (MDA-MD-231), which expressed endogenously high level of TF. In our examination of the mechanism by which aPL stimulation leading to TF up regulation, we have discovered that microRNAs (miRs) play a significant role. Using the two cells with different endogenous expression of TF, we showed that miR106b is highly expressed in MDA-MB-468 compared to MDA-MB-231. Treatment of MDA-MB-468 with miR106b inhibitor released the inhibition of TF expression suggesting that miR106b negatively regulate TF expression. Our preliminary data show that aPL modifies miR106b expression in MDA-MB-468.

CHED 193

Interaction of mitochondrial DNA with RHPS4

Irene Xiang1, [email protected], Brett Anthony Kaufman3, Liliya A. Yatsunyk1. (1) Chemistry and Biochemistry, Swarthmore College, Swarthmore, Pennsylvania, United States (3) Vascular Medicine Institute University of Pittsburgh, Pittsburgh, Pennsylvania, United States

Quadruplexes (GQ) are non-canonical tetra-stranded DNA structures implicated in cancer and aging. Recent evidence indicates that mitochondrial DNA can fold into GQ structures [1], suggesting that GQs can affect mitochondrial genome stability. We have investigated the interactions between the well-known quadruplex ligand, RHPS4, with two different mitochondrial G-rich DNA sequences, oligo A and B, through CD melting and UV-vis titration experiments. 10 μM RHPS4 is found to stabilize these oligonucleotides by 7.9 ± 1.0 °C and 14.6 ± 0.8 °C. In the case of oligonucleotide A, RHPS4 decreases observed hysteresis from 32.4 to 19.5 °C suggesting that folding process for oligonucleotide A is kinetically slow and the presence of ligand speeds up this slow kinetics. Upon titration of RHPS4 with GQs formed by each Oligo A and by Oligo B, similar red shifts and hypochromicities are observed. At 510 nm, Oligo A had a red shift of 11.5 ± 0.2 with a % hypochromicity of 22 ± 2 while Oligo B had a red shift of 11.6 ± 0.5 and % hypochromicity of 23 ± 2. These rather high values suggest significant overlap between the p-systems of RHPS4 and the G-tetrad, and thus indicate close interactions, most probably end-stacking. Our data suggest that RHPS4 binds Oligo A with a 3:1 stoichiometry and a binding constant of (0.5 ± 0.3)×106 M-1. In contrast, RHPS4 binds with Oligo B with a 2:1 stoichiometry and very similar binding constant, (0.5 ± 0.1)×106 M-1. The ability of RHPS4 to bind and stabilize Oligo A and B has biological importance in mitochondrial anti-cancer agents.

CHED 194

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Atomic force microscopy measurements of breast cancer cells treated with single walled carbon nanotubes

Mathiu Perez1, [email protected], Lorena Ulloa1, [email protected], Sunil Dehipawala2, Tirandai Hemraj Benny3, Regina Sullivan1. (1) Biological Sciences and Geology, Queensborough Community College, Bayside, New York, United States (2) Physics, Queensborough Community College, Bayside, New York, United States (3) Chemistry, Queensborough Community College, Bayside, New York, United States

Biomedical applications of single walled carbon nanotubes (SWCNT) have the potential to expand treatment options for cancer patients. However biosafety studies are currently inconclusive. These studies have been limited by technical issues related to the hydrophobic nature of the nanotubes. The diameter (1.5 nm) of the nanotube should allow passage through cellular gap junctions and ion channels but aggregation of the nanotubes in aqueous solutions decreases cellular uptake in in vitro studies. Coating single walled carbon nanotubes with collagen has been shown to facilitate cellular uptake thus allowing for intracellular associations to be investigated. In this study, MDA-MB 468 cells were treated with collagen coated SWCNT. Atomic Force Microscopy was used to determine if the coated nanotubes were entering the breast cancer cells. Migration assays were performed and revealed that breast cancer cells treated with collagen coated SWCNT have a reduced rate of migration. These results suggest that the SWCNT may be incorporating into the actin cytoskeletal disrupting rearrangements that are required for the metastatic process. In future studies we plan to measure Young’s modulus which is an indicator of the degree of flexibility which in turn can be correlated with changes in the actin cytoskeleton. The study will be expended to include other types of cancer cells as well noncancerous cells and may reveal potentially novel cancer treatments.

CHED 195

Geis Digital Archive: An Open-Access Educational Resource for Structural Biology

Christopher Markosian1, [email protected], Belle Lin1, [email protected], Stephen Burley3,2, Christine Zardecki3, Alexander Alvarado4, Nicole Werpachowski5. (1) Molecular Biology and Biochemistry and Center for Integrative Proteomics Research, Rutgers, The State University of New Jersey, Piscataway, New Jersey, United States (2) Skaggs School of Pharmacy and Pharmaceutical Sciences and San Diego Supercomputer Center, University of California, San Diego, La Jolla, California, United States (3) RCSB PDB, Department of Chemistry and Chemical Biology, Center for Integrative Proteomics Research, Rutgers, The State University of New Jersey, Piscataway, New Jersey, United States (4) University of Southern Califonia, Los Angeles, California, United States (5) Fordham University Lincoln Center, New York, New York, United States

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X-ray crystallographers began to decipher the structures of proteins at the level of individual atoms in the late 1950s. Irving Geis (1908-1997), a pioneer in scientific illustration, created the hand-drawn molecular images seen by generations of scientists in scientific journals and textbooks. Through a collaboration with the Howard Hughes Medical Institute, the RCSB Protein Data Bank has established a digital archive of Geis' molecular art at http://pdb101.rcsb.org that displays his illustrations in the context of the experimental data and related molecular information. Each image has been annotated with molecular information and connected with the primary experimental data contained in the PDB. Using this resource, visitors can learn about molecular structure and function, interactively view the molecule in 3D, and download Geis’ work for non-commercial usage. RCSB PDB is funded by the NSF (DBI-1338415), NIH, and the DOE.

CHED 196

Transformation of the organic chemistry laboratory: Assessment of instructor practice and meaningful learning in a modular organic laboratory sequence

William Marmor1, [email protected], Rodgers Kipsang1, [email protected], Kathryn Miller1,2, Thomas D. Kim1. (1) School of Chemistry and Materials Science, Rochester Institute of Technology, Rochester, New York, United States (2) University of Nebraska-Lincoln, Lincoln, Nebraska, United States

We will present assessments for a full implementation of an innovative macroscale organic chemistry lab module sequence. An overview of these novel organic lab modules will be presented and their assessment via the Reformed Teaching Observational Protocol (RTOP) and Meaningful Learning in the Laboratory Instrument (MLLI) will be outlined. Results from these assessments will be used to inform the impact of these laboratory modules within the framework of transferability of the modules between different instructors and the transportability of the modules between different institutions. Additionally, data from the MLLI will be used to analyze the impact of these modules on student affect and cognition.

CHED 197

Multistep synthesis for second year organic students: Wittig olefination, transfer hydrogenation, and ester hydrolysis

Patrick A. Ross1, [email protected], Susan Ragheb2, Michael J. Castaldi1, James K. Murray1. (1) Chemistry, Immaculata University, Immaculata, Pennsylvania, United States (2) Chemistry, St. Peter's University, Jersey City, New Jersey, United States

In second semester organic chemistry, many different reactions are introduced to students. However, many students see these reactions as individual steps to convert one material to the next. In doing so students do not see how the reactions are put

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together to make a final product which is the way organic chemistry is practiced. By investigating three fundamental reactions the students are able to observe the way that the product of one reaction can be used as the starting material for the next.

CHED 198

Perception of Harm of Prescription Drugs Among College Students Based on a Student's Home State and Education Level

Jason A. Burch, [email protected], Mary E. Railing. Chemistry, Wheeling Jesuit University , Wheeling, West Virginia, United States

The purpose of this research is to identify college students' perception of harm and availability of prescription opioids, mainly Vicodin. The main focus of the research is to discover whether students’ home state and level of science/healthcare education play a significant role in these perceptions. We hypothesized that students from states with lower prescription drug abuse would be more knowledgeable. Through this research, our goal is to make college students more aware of prescription drug abuse and common conceptions/misconceptions about prescription drugs. This research was conducted by collecting data by means of anonymous surveys from students who attend Wheeling Jesuit University. The results of the perception questions are then tested against the home states and education level. With prescription drug abuse being an increasing problem in the Ohio Valley, it seemed fitting to see how college age students perceived prescription drugs. Students were asked questions such as where they thought people acquired prescription opioids, other than from a prescription, as well as various insights on the percentage of people using/abusing prescription opioids, mainly Vicodin. The data will be analyzed and final conclusions will be drawn on how a student’s home state and education level influences the perception of harm of prescription opioids. The implications of this research are to make the general population more aware of the perceptions of college age students about prescription drug abuse. It could also serve as a tool to design better future programs about raising awareness of prescription drug abuse in the university setting.

CHED 199

Use of selective TOCSY NMR experiments for quantifying menthone/menthol ratio in the organic synthesis lab

Leyu Zhang1, [email protected], Judy Fang2, [email protected], Aaron Hogan2, [email protected], Elisabetta Fasella2, Maria C. Tettamanzi2. (1) Pharmacy, University of the Sciences, Philadelphia, Pennsylvania, United States (2) Chemistry and Biochemistry, University of the Sciences, Philadelphia, Pennsylvania, United States

The oxidation of menthol to menthone using Oxone, a greener alternative to chromium-based oxidants, was investigated. The experiment was based on a published procedure

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for the oxidation of borneol to camphor using Oxone and sodium chloride. This reaction affords camphor cleanly and in high yield. We found that under the same conditions used for the oxidation of borneol, menthol only gave partial oxidation to menthone. Increasing the amount of sodium chloride catalyst or of Oxone, and lengthening the reaction time still resulted in only partial oxidation. We found the use of TOCSY NMR very convenient to monitor and quantify the ratio of menthol and menthone in the reaction mixture. The ratio of menthol to menthone was determined without the aid of any chromatographic purification step by using a very short 1D selective TOCSY experiment. This NMR technique has been reported as a quantification method of minor components in complex mixtures. We found the selective TOCSY very appealing for a teaching lab experiment in which the students can readily distinguish and quantify the components in a reaction mixture. The conventional use of 1H NMR to quantify reaction mixtures is sometimes discouraging, because for similar compounds often only a few downfield signals appear clearly separated, and the rest are superimposed and not suitable for quantification. We found the TOCSY experiment to be a rapid and efficient method that overcomes the limitations of conventional 1H NMR for analysis of this reaction mixture.

CHED 200

Eugenol isolation and derivatization for incorporation into a synthesis laboratory

Kenton Mummert, [email protected], Steven M. Kennedy. Chemistry, Millersville University of Pennsylvania, Millersville, Pennsylvania, United States

A quick and economical pressurized hot water extraction method for the isolation of Eugenol from cloves, based on the work of Just and coworkers, is currently being optimized for incorporation into an upper-level undergraduate organic synthesis laboratory. The Just method takes advantage of a commercially available espresso machine to facilitate the natural product extraction. The synthesis of an Eugenol derivative [(E)-4-(4-hydroxy-3-methoxyphenyl)but-2-en-ol] based on the Grubb’s Cross Metathesis of Eugenol and cis-2-butene-1,4-diol, reported by Taber and coworkers, is being explored. Students will use the derivative as the starting material for a four-week multi-step synthesis laboratory that they design. During the first half of a sixteen-week semester, students will use SciFinder to help them plan their multi-step synthesis.

CHED 201

Baeyer-Villiger investigative experiment for the undergraduate organic chemistry laboratory

Beth Withrow1, [email protected], Jacqueline Killen2, [email protected], David L. Dillon1. (1) Chemistry, Colorado State University - Pueblo, Pueblo, Colorado, United States (2) Colorado State University Pueblo, Colorado Springs, Colorado, United States

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The Baeyer-Villiger reaction (B-V) is an important reaction for oxidation of aldehydes and ketones that is omitted from many popular undergraduate organic laboratory textbooks. The reaction uses an oxidizing agent, such as hydrogen peroxide, trichloroperoxyacetic acid, or m-chloroperoxybenzoic acid to insert oxygen adjacent to the carbonyl carbon. The insertion involves an initial attack by the nucleophilic peroxy oxygen group followed by a rearrangement involving migration onto the inserted oxygen. The B-V reaction has been studied both experimentally and computationally in order to better understand the mechanism by which the ester products are formed. It is well-established that highly substituted carbons (tertiary carbons) migrate better than less substituted carbons (secondary or primary), but the migration of substituted phenyl groups depends on the nature of the substituent. Specifically, it is known that p-methoxyphenyl groups migrate better than tertiary carbons, and even better than hydrogen (the latter in B-V reactions of p-methoxybenzaldehyde). This project focuses on B-V reactions carried out in the undergraduate organic chemistry laboratory using variously substituted phenyl ketones and phenyl aldehydes and various oxidizing agents in an exploration of the migratory aptitude of groups.

CHED 202

Chemical upcycling of guaifenesin: An experiment for organic chemistry labs

Katarzyna Maziarz, [email protected], Homar S. Barcena. Kingsborough Community College, New york, New York, United States

Guaifenesin is the active ingredient for over-the-counter cough medicines such as Mucinex. In our effort to repurpose expired guaifenesin tablets, we are developing experimental protocols for the Organic Chemistry instruction that utilizes the functional group transformations possible for this drug. We exploit the phenol moiety, as well as the vicinal diols to develop chemistry that is amenable to teaching labs. In so doing, we engage student interest in green chemistry and raise awareness of drug pollution.

CHED 203

Chemical upcycling of paracetamol: An experiment for organic chemistry labs

Michelle Barrie, [email protected], Homar S. Barcena. Kingsborough Community College, New york, New York, United States

Paracetamol is among the most popular over-the-counter drugs used to treat pain and fever, although it has been recently reported to elevate the risk of heart attacks. In an effort to repurpose expired paracetamol, we are developing an experiment for Organic Chemistry instruction that explores the electrophilic aromatic substition of the active ingredient extracted from an expired tablet. Our aim is to engage students in green chemistry and raise awareness of drug pollution.

CHED 204

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College students’ perceptions about commonly abused prescription drugs

Brenna Becca, [email protected], Emily L. Dalton, Mary E. Railing. Chemistry, Wheeling Jesuit University , Wheeling , West Virginia, United States

The purpose of this research is to compare college students’ perceptions of harm and availability of two classes of prescription drugs commonly abused, namely stimulants and opioids. With prescription drug abuse being an increasing problem, particularly in West Virginia, it seemed pertinent to see how college age students perceived the harm and availability of prescription drugs. The main focus of the research is to discover whether a student’s major and level of science and/or healthcare education plays a significant role in these perceptions. We hypothesized that students with more science or healthcare education would be more knowledgeable about prescription drug hazards. This research was conducted by collecting data from students who attend Wheeling Jesuit University by means of two anonymous surveys. The results of the perception questions were then tested against the student’s major and level of science or health care education. Students were asked various questions including where they thought people acquired prescription drugs illegally, as well as various insights on the percentage of people using/abusing prescription stimulants like Adderall or opioids like Vicodin. Through this research, our goal is to make college students more aware of prescription drug abuse and common conceptions/misconceptions about prescription drugs. It could also be used as a tool to design better future programs about raising awareness of prescription drug abuse in the university setting.

CHED 205

Impact of professional development programs on middle and high school teachers’ instruction in chemistry: Findings from a five-year longitudinal study

Abraham A. Williams1, [email protected], Adrian J. Contreras1, [email protected], Richard Lewis2, Edward E. Gonzalez3, Bonnie McCormick4, Alakananda R. Chaudhuri3. (1) University of the Incarnate Word, San Antonio, Texas, United States (2) Sociology, University of Texas at San Antonio, San Antonio, Texas, United States (3) Chem Dept, Univ of The Incarnate Word, San Antonio, Texas, United States (4) Biology, University of the Incarnate Word, San Antonio, Texas, United States

This study examines the effects of a university-based professional development program focused on chemistry content, pedagogical content knowledge, incorporation of inquiry activities, and implementation of cooperative learning strategies for middle and high school science teachers in discrete cohorts (N = 80) over a period of five years. The professional development programs are funded by the Teacher Quality Grant Program (TQGP) “to promote improved instruction in mathematics and science for Texas school children by providing professional development for their teachers.” The program evaluation method used longitudinal data collected from pre and post-test content knowledge assessments, revised inquiry-based lesson plans, classroom observations, peer observations, reflective journals, focus group discussions and

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surveys. Analysis of the data indicates a significant change in participant content knowledge and a consistent pattern of change in classroom teaching practices in all cohorts. Furthermore, we found that the incorporation of inquiry-based cooperative learning activities increased the use of these teaching methods in the participants’ classrooms.

CHED 206

Measuring students’ understanding of periodic trends when using multiple representation of the trends and atomic structure

Victoria Kaloudis, [email protected], Kathryn Balnius, Patrick L. Daubenmire, Philip Nahlik, Linda C. Brazdil. Department of Chemistry and Biochemistry, Loyola University Chicago, Chicago, Illinois, United States

This investigation focused on students’ understanding of periodic trends when using multiple representations of the periodic table of elements in general chemistry classrooms. The relationship of structure to repeating patterns of properties is a critical foundational concept in chemistry. The research group sought to answer the question: If graphic or visual alternative representations of the Periodic Table of Elements are used in teaching specific trends, will they enhance students’ knowledge and ability to describe reasons for those trends? Each participant was presented with a pre-test, in which the participant engaged in a think aloud interview through a set of problems involving periodic properties. During their problem solving, a Tobii eye tracker instrument recorded eye movements and gaze patterns on the problem and trend representations. Participants were then grouped by stratified random sampling and received one of three sets of lessons: (1) no representations in addition to the periodic table, (2) additional representations, but no reference to them in the lessons, or (3) additional representations and reference to them during the lessons. After all lessons were over, each participant returned for a post-test and second think aloud interview. Researchers compared each student’s pre-test and post-test results and measured how using different variations of the periodic table may or may not support students’ understanding of periodic trends. The research group found that both types of majors showed improvement from the pre-test to the post-test, but have not yet detected differences between or within groups.

CHED 207

Using classroom engagement to impact campus recycling systems

Manisha Nigam1, [email protected], Amy Buxbaum2. (1) Chemistry, University of Pittsburgh at Johnstown, Johnstown, Pennsylvania, United States (2) Finance and Administration, Pitt-Johnstown, Johnstown, Pennsylvania, United States

This presentation describes the implementation of a campus-wide single stream recycling program that makes recycling easy and effective for all university citizens. This

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presentation summarizes the current status of the program, as well as the implementation challenges we are facing. The program was conceived within the context of a Green Chemistry & Sustainability course, where we are using real-world contexts to engage student learning. In this course, students identified and proposed various projects to understand the chemistry that underlies environmental, societal, and personal health issues that are critical for a sustainable future for the entire campus. The viability of these projects was analyzed by students in conjunction with the campus administration; and it was discovered that basic recycling via sorting was ineffective across the campus. The decision to implement single stream recycling was then driven by the student body with the financial support from the administration.

CHED 208

Modern techniques in biochemistry education: Analysis of bovine pancreatic trypsin inhibitor using HPLC

Matthew Steinsaltz, [email protected], Ryan Carpenter . Chemistry , SUNY Geneseo, Bronx, New York, United States

In the undergraduate curriculum, the use of High-Performance Liquid Chromatography (HPLC) with respect to proteins is very often used for purification purposes; however, there is potential for its use in protein and peptide structural analysis. We are in the process of developing a novel biochemistry laboratory experiment that will investigate structural modifications of Bovine Pancreatic Trypsin Inhibitor (BPTI) using a C18 Reverse Phase HPLC (HPLC-RP) column. BPTI is a 6.5 KDa protein (58 amino acids) and contains three intramolecular disulfide bonds. HPLC has been employed to distinguish the following: native BPTI (completely folded), denatured BPTI (partially unfolded), and denatured and reduced BPTI (completely unfolded). For these experiments, Mass Spectrometry (MS) is the primary detection method. A gradient separation was employed (mobile phase: acetonitrile, and water each with 1% TFA), and acetonitrile concentration was increased from 10% to 50% over 25 minutes (35-minute run time). The results indicate that the three different forms of the protein have distinct elution times, with the most folded form eluting earliest at approximately 8 and 15 minutes, and the most unfolded eluting last at approximately 24 minutes. Once established, this project can further be developed into an upper-level undergraduate biochemistry laboratory experiment that will provide students with a deeper understanding of protein structure, oxidation/reduction, and a hands-on experience with HPLC.

CHED 209

Effectiveness of peer led supplements in an undergraduate general chemistry course based on test scores

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Allison S. Logsdon1, [email protected], Mary E. Erickson1, Lynn Villafuerte2, Joseph A. Heppert3. (1) Chemistry, University of Kansas, Lawrence, Kansas, United States (2) Office for Diversity in Science Training, University of Kansas, Lawrence, Kansas, United States (3) Office of Research and Graduate Studies, University of Kansas, Lawrence, Kansas, United States

Both university educators and students tend to agree improved learning techniques are long overdue, particularly in STEM (science, technology, engineering, and math) fields. Many options to enhance STEM learning have been explored, and one of the most promising strategies involves supplemental peer led problem-solving sessions. This study summarizes the effect of peer learning session on student examination scores in a general chemistry course at the University of Kansas. The course included weekly problem-solving sessions offered through the PLUS (peer-led undergraduate supplements) program. PLUS sessions utilized inquiry questions based on the previous week’s material. Students were encouraged to collaborate with their peers and the PLUS student leaders in order to solve this packet. Exam scores for students who attended these sessions were compared with those of students who did not engage in the PLUS program. A two-tailed t test assuming unequal variance run on Exam 1 data revealed a statistical difference between students who attended these additional sessions (N=81, M=78.9, S=13.4) and those who did not (N=759, M=74.9, S=14.4), t(759)=-2.498, p=0.014, a= 0.05. Similar results were observed for Exam 2: students who attended (N=82, M=80.8, S=16.2) and students who did not attend (N=732, M=73.3, S=17.6), t(732)=-3.909, p=0.0002, a= 0.05. These results seem to indicate a positive correlation between participation in peer led study sessions and exam performance; however, a similar test run on Exam 3 data did not reveal a statistical difference between students who attended these additional sessions (N=105, M=66.7, S=15.3) and those who did not (N=686, M=64.0, S=17.4), t(686)=-1.664, p=0.098, a= 0.05.

CHED 210

Integrating energy in the laboratory for engineers and scientists

Kathryn Notarangelo, [email protected], Eleazar Bernal, Juan Jaramillo, Jessica Torres, Ruifan Pei, Elizabeth Mule, Johanna Tang, Reginaldo Gomes, Dayannara Muñoz, William Livernois, Faben Girma, Emma Valentine, Zi-Ning Choo, Pragya Tooteja, Casey Crownhart, Timothy Manganello, Jonas De Oliveira, Anita Wamakima, Konyin Oluwole, Alexander Kendrick, Jean-Francois P. Hamel. Chemical Engineering, Massachusetts Institute of Technology, Cambridge, Massachusetts, United States

In the coming years, rapid innovation in developing clean energy supplies is essential as a whole-scale shift to low-carbon energy supplies is key to avoiding dangerous levels of climate change. In response to this global issue and corresponding increase in student interest in energy, MIT’s Energy Initiative is working to include new energy topics into classrooms and laboratories, campus wide. To this end, the Chemical-Biological Engineering Lab course is now enabling students to conduct energy-related

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research, and to bridge research programs and hands-on practice into the conventional program. In partnership with the National Renewable Energy Laboratory, two projects were launched in the laboratory this year, using an integrated bioprocess-mass spectrometry platform. The first project uses biorefinery waste to produce muconic acid from lignin-derived target molecules, by recombinant Pseudomonas putida. Muconic acid is a high value-added product for manufacturing new functional resins, bio-plastics, food additives, agrochemicals, and pharmaceuticals, and it boots indirectly the economic viability of the biofuel process. The second project focuses on optimizing conditions for the aerobic cultivation of oleaginous yeast strains, to produce triacylglycerol fatty acids. These fatty acids are analyzed through methylation and used as a precursor to renewable biodiesel.

CHED 211

Investigating the antimicrobial properties of brominated parabens: An organic laboratory experience

Hailey Kintz, [email protected], Shelby Furman, Jonathan Bietsch, Andrew A. Yeagley. Chemistry & Physics, Longwood University, Farmville, Virginia, United States

This work is attempting to create a laboratory course for second semester organic lecture that maintains the synthetic elements currently present and incorporates an inquiry based project. The students will prepare brominated paraben derivatives and screen them for activity against a bacterium. These class data will then be used to generate a course-wide structure-activity analysis (SAR). In preparation of this course we have optimized a 5 step synthesis towards these parabens and began screening various target parabens against applicable bacterium. We have found a multitude of gram-positive bacteria that illustrate SAR responses that can be used within the course.

CHED 212

Characterization of ice nucleation at mineral surfaces

Zachary Graziano, [email protected], Diana Slough, Yu-Shan Lin. Chemistry, Tufts University, Medford, Massachusetts, United States

Heterogeneous ice nucleation occurring on mineral dusts in clouds plays an important role in climate. While the ice nucleating activity of several minerals has been experimentally investigated, the features of specific minerals that enable them to exhibit increased nucleation ability over others have yet to be identified. Moreover, the molecular-level mechanisms by which ice nucleation occurs at mineral surfaces largely remain uncharacterized. Here, we use molecular dynamics simulations to investigate water behavior at the surfaces of a number of minerals. From the results of these simulations, we have gained insights into surface features affecting ice nucleation that may be used to inform the design of hyperactive ice nucleating agents.

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CHED 213

IR spectrum prediction and analysis by PED determination using unified group theory of two sulfur-containing molecules: Digermylsulfide and divinyl sulfoxide

Joshua M. Mukerjee1, [email protected], Yasin Al Fahham2, [email protected], Hae-Won Kim1. (1) Chemistry, Penn State Abington, Abington, Pennsylvania, United States (2) Chemistry, Penn State University Park, University Park, Pennsylvania, United States

We predict IR frequencies and their normal mode assignments for digermylsulfide (C2v) and divinyl sulfoxide (Cs). We evaluate normal mode assignments with potential energy distribution (PED) determinations. The IR frequency calculations are performed at DFT/B3LYP methodology. The 6-311G** basis set is used for both molecules. IR spectra of ground states are calculated by the use of program Gaussian 09 and PED determination of normal modes are determined by the use of vibrational analysis program MOLVIB. We compare our theoretical results with published experimental infrared spectra. The Internal symmetry coordinates are generated using Kim’s Correspondence Rules of unified group theory.

CHED 214

Molecular dynamics simulations of a series of experimentally active ligands bound to fatty acid binding protein 5

Brendan Brown, [email protected], Chrystal D. Bruce. Chemistry, John Carroll University, University Heights, Ohio, United States

Fatty Acid Binding Protein 5 (FABP5) naturally binds retinoic acid and is important in cell growth. It provides an important target for cancer therapies, and as such, was subjected to a screening procedure where a series of small molecules were determined to be active upon binding FABP5. The variety of structural features of these ligands brings into question the binding mechanism for ligand recognition. Previously, we have used docking software to dock these ligands in the binding pocket of FABP5. In the work presented here, the binding mechanism is explored using the molecular dynamics software package Amber14.

CHED 215

Molecular dynamics studies of the binding of retinoic acid to the transport protein CRABP-II

Nathanael Hunter, [email protected], Chrystal D. Bruce. Chemistry, John Carroll University, University Heights, Ohio, United States

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Treatment of cancer cells with retinoic acid (RA) can either lead to proliferation or inhibition of growth of the cells depending on the relative ratio of two proteins in the cancer cell: fatty acid binding protein 5 (FABP5) and cellular retinoic acid binding protein II (CRABP-II). It has been suggested based on experiments that CRABP-II has a higher affinity to RA than FABP5. The goal of this project was to examine the binding of retinoic acid in the binding pocket of CRABP-II in a molecular dynamics simulation. Results of the molecular dynamics production run, performed using AMBER12 software, as well as free energy approximations, calculated using molecular mechanics/generalized born surface area and normal mode harmonic entropy approximations, will be presented. These will be compared to preliminary docking results found using AutoDock Vina docking software, as well as the results found for the binding of FABP5 and retinoic acid.

CHED 216

Computational investigation of solvent effects on the reactivity of C-amino-1,2,4-triazoles

Jessica K. Niblo, [email protected], Robert J. Olsen. School of Natural Sciences and Mathematics, Stockton University, Galloway, New Jersey, United States

The dependence of reactivity indices of C-amino-1,2,4-triazoles on the identity of the solvent is investigated computationally. Emphasis is placed on identifying models that are minimal with respect to theory level and basis set size yet give robust trends in reactivity index within the framework of a continuum solvation model (COSMO, as implemented in NWChem).

CHED 217

Proton affinities of proline dipeptides

Paul Arcoria, [email protected], Jennifer Poutsma. Chemistry & Biochemistry, Old Dominion University, Norfolk, Virginia, United States

The proton affinities of the amino acids have been thoroughly investigated. However, only a few studies have been conducted on small peptides. A next step in understanding the intrinsic properties of proteins is to determine how the proton affinities of dipeptides differ from those of amino acids. Many of the systematic trends in basicity of amino acids rely on the basicity of the amino terminus, which will be converted to an amide when the amino acids are inserted into the middle of small peptides. Furthermore, how will the possibility of new hydrogen bonds effect the behavior of the dipeptide compounds? As a first step, a systematic study of the proline dipeptides (XPro and ProX) will be undertaken. The proton affinities of the XPro dipeptides could provide insight into the proline effect observed in tandem mass spectrometry. The proton affinities of the dipeptides will be determined via ab initio calculations and the site of protonation will be identified. The geometries will be

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optimized at the B3LYP/6-31+G(d) level of theory and energies will be calculated using B3LYP/6-311++G(d,p). In addition, these results will be compared to experimental values obtained using mass spectrometry and the kinetic method

CHED 218

Arsenic removal using biosand filters amended with iron nails: Effect of pH

Anjni Patel, [email protected], David J. Temme, Jean M. Smolen. Chemistry, Saint Joseph's University, Philadelphia, Pennsylvania, United States

Despite awareness of the health consequences that result from ingesting arsenic-tainted water and the efforts that have been made to implement technologies to remove arsenic from affected groundwater, there are still populations throughout the world that are contending with poisoned water and no practical solution. Research efforts in the Department of Biology and the Institute of Clinical Bioethics as Saint Joseph’s University have demonstrated the effectiveness of a slow sand water filter on the removal of E. coli from contaminated water. This simple design employs nested plastic buckets containing cheesecloth, gravel and sand. The same filter design was evaluated for its effectiveness in removing arsenic from water. In our research group, we have assessed the effect of pH and filter design on removal efficiency. Iron nails were added in a single layer to some filters to evaluate this effect on arsenic removal. Influent concentrations of arsenic were also varied as part of the experimental design. Water aliquots were analyzed for arsenic concentrations using Inductively Coupled Plasma (ICP) spectroscopy. Initial results illustrate that this simple water filter design may be effective at removing arsenic to accepted levels of 10 ppb, especially for low influent concentrations and aqueous pH near 7.

CHED 219

Developing a reactive ink for marker-based identification of treated and untreated waste lumber

Michael Bagley, [email protected], John L. Ferry . Chemistry and Biochemistry, University of South Carolina, Columbia, South Carolina, United States

Approximately 12.6 million tons of structural wood is disposed of in landfills annually. Wood used in outdoor construction is often made rot resistant by application of fungicides and insecticides. Historically these have included tar, halophenols and mixtures of chromium, arsenic and copper. Recycling or reuse of structural wood products is limited by the possibility of human contact with recycled rot-resistant wood. Aged wood treated with organic preservatives is readily identifiable by visual inspection but aged metal treated wood identification is less straightforward. Historically metal-based treatment schemes have focused mixtures of elements but Cu has been common to these techniques for over 50 years. Here we report a qualitative and quantitative technique for Cu(II) analysis on the surface of wood products based on the application

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of a Cu(II)-sensitive ink amenable for swipe testing with a felt marking pen. A pH and antioxidant-optimized solution of Chromazurol-S was developed based on the response of the indicator to Cu(II) ions in aqueous solution and applied to a NIST standard reference wood product (8493). The most effective pH adjustor as a function of sensitivity was phosphate (pH 5, monobasic) and the most effective antioxidant (longevity) was butylated-hydroxy toluene (BHT, 1.82 mM). Detection limits were in the low ppm range visually. Quantification was performed by spectral analysis of images of the treated wood comparing the blue band of the indicator absorbance against that of a standard, barium sulfate. Images were obtained on a GoPro III and analyzed in Adobe Illustrator. Quantification was also in the ppm range. The ultimate goal is the production of a smartphone app to analyze pictures taken roadside for better decision-making in wood reclamation.

CHED 220

Analysis of metal ions in rivers at Texas state parks using inductively coupled plasma-mass spectroscopy

Adrian J. Contreras1, [email protected], Abraham A. Williams1, [email protected], Patricia P. Gonzalez2, Alakananda R. Chaudhuri1, Edward E. Gonzalez1. (1) Chemistry and Biochemistry, University of the Incarnate Word, San Antonio, Texas, United States (2) San Antonio Water Supply, San Antonio, Texas, United States

The purpose of this study is to analyze the river water flowing through Texas state parks for total metal content and check the levels of toxic elements following EPA methods. Water samples were taken from the 1) Frio river at Garner State Park near Concan; 2) Llano river at South Llano River State Park near Junction; 3) Nueces river near Devil’s Sinkhole State Natural Area in Rocksprings; and 4) Sabinal river at Lost Maples State Natural Area near Vanderpool. Water samples were collected in 1 liter polystyrene bottles and immediately preserved with (1 + 1) nitric acid and later filtered in the lab through a 0.45 µm filter. Samples of 100 mL were digested by EPA method 200.8. Water samples were analyzed for twenty-seven metals by ICP-MS using a Vairan 820-MS model and the results compared to EPA limits for recreational water. Future studies will analyze organic contaminants for toxic levels.

CHED 221

Use of native plants in removing nitrates from waste water

Maire F. Austin, [email protected], Scott Lopez, Mary E. Railing. Chemistry, Wheeling Jesuit University, Wheeling, West Virginia, United States

The significance of this study was to use plants to lower the nitrate concentration found in the runoff of the Wheeling Water Treatment Center. The concentration of nitrates being unleashed into the Ohio River from the Wheeling Water Treatment Center was

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above 1 ppm which is a high enough to accumulate and cause negative environmental impacts. Phytoremediation is the use of plants for in situ treatment of polluted land areas. In order to determine this affinity for nitrate absorption in the plants, they were tested in a hydroponics system. Soy bean plants were chosen to clean up the water because of their efficiency in the nitrogen cycle of converting nitrates into environmentally friendly nitrites, which can be more easily accepted by the Ohio River ecosystem. The soy beans were grown in a Crop King Hydroponic System where the roots are in a stream of nutrient water. Measurements of pH, conductivity and nitrate concentration of the recycling water were taken weekly. The analytical technique used for determining the nitrate concentration was the Lamotte Nitrate Testing method while the pH and conductivity were found using a portable electrode. Over a period of roughly a month the conductivity and the pH steadily increased until the plants died. The determination of the nitrates concentration did not yield any results since the method implemented was not sensitive enough for detecting a change in concentration. The next step in improving this research is to use native plants in Wheeling as well as using a more sensitive analytical technique.

CHED 222

Detection of pesticides in locally produced honey

Victoria Kompanijec, [email protected], Christopher Kubow, Jay Charlebois. Chemistry, State University of New York at Geneseo, Geneseo, New York, United States

Colony collapse disorder and other diseases have caused the honey bee population to plummet in past years. Many people believe that pesticide use is a contributing factor to this decrease. We aim to develop a simple and efficient method of detecting trace amounts of pesticide in honey samples. Samples are prepared using the QuEChERS (Quick, Easy, Cheap, Efficient, Rugged and Safe) method and run through an HPLC to obtain a mass spectrum. We have optimized an HPLC-MS method for examining honey samples. These honey samples are obtained from local sources around New York State. We hope to be able to gauge the level of pesticide exposure of honey bees to pesticides in the environment.

CHED 223

Absorptive properties of atmospheric aerosols collected in Towson, MD

Ana Morales, [email protected], L. E. Meade, Kathryn E. Kautzman. Chemistry, Towson University, Towson, Maryland, United States

Organic aerosols account for a substantial fraction of total aerosol mass and have significant impacts on the warming and cooling of the atmosphere that have yet to be fully defined. In most cases, aerosols scatter radiation leading to an overall cooling effect. However, certain classes of compounds such as HULIS, nitrogen- and sulfur

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containing species, soot, and products from biomass burning have been found to contribute to the absorption of radiation, leading to atmospheric warming. The aerosols in this study were previously collected on filters from the top of Glen Tower A at Towson University. These filters were divided into small sections so that multiple analyses can be performed. The filters are sonicated using a solvent of 50/50 DCM/MeOH, filtered, and dried down using a gentle stream of N2. The samples are then reconstituted in 5 mL of the 50/50 DCM/MeOH solution and the absorptive properties are measured using UV-Vis photospectrometry. We find significant absorption in both the visible, 400 nm-700 nm, and near UV regions, 200 nm-400 nm, of the spectrum corresponding to absorption from black carbon (BC) and brown carbon (BrC), respectively. To quantify the absorptive properties, the mass absorption coefficient (MAC) for each filter is determined. We present seasonal trends in the absorptive properties and correlate the absorptive properties with known tracer species using ultra performance liquid chromatography coupled with mass spectrometry (UPLC/MS).

CHED 224

Cleaning and protecting the water we use via NYC’s wastewater treatment system & DEP Shoreline Survey Unit

Irene Sun1, [email protected], Jorge Villacis2, Faye Jacques2, Panayiotis Meleties4, Paris D. Svoronos1. (1) Chemistry, Queensborough Community College, Bayside, New York, United States (2) New York City-Division of Environmental Protection, Wards Island, New York, United States (4) Office of the Provost, York College, Jamaica, New York, United States

In order to sustain the supply and demand of water usage for all NYC residents, the Department of Environmental Protection (DEP) has fourteen wastewater treatment plants located throughout the five boroughs of New York City (Bronx, Brooklyn, Manhattan, Queens and Staten Island). Each treatment plant recycles wastewater from the sanitary sewer lines (from homes, businesses, schools, etc.) where the resulting clean water is discharged back into the NYC rivers. A detailed five step process regarding the treatment of wastewater will be presented. Likewise the NYC DEP Compliance Monitoring Section (CMS) is comprised of two sectors – Industrial Pretreatment Program (IPP) and Shoreline Survey Unit (SSU). SSU aggressively pursues field investigations necessary to locate and terminate illegal contaminated discharges to NYC waters from outfalls throughout the tristate area. Different investigational methods will be examined and also presented.

CHED 225

Determination of pesticides in fruits, vegetables and grains via the Luke method

Irene Sun1, [email protected], Keeshan Williams2, Michael Iorsh3, Paris D. Svoronos1. (1) Chemistry, Queensborough Community College, Bayside, New York, United States (2) Chemical and Biological Engineering, The Polytechnic Institute of

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NYU, Brooklyn, New York, United States (3) Food and Drugs Administration, NE Region, Jamaica, NY, Jamaica, New York, United States

The classic procedural methods used to determine residual pesticide levels in food generally tend to be labor intensive, require significant volumes of organic solvents and result in the production of large quantities of hazardous waste. The Luke method, which was introduced in 1981, uses an extraction procedure that is performed three times for maximum pesticide recovery. Minimal amount of solvents are used with low production levels of hazardous waste. The method is comprised of two groups – Section 302 and C6: SAX/PSA Cartridge Cleanup. Section 302 involves extraction with acetone, liquid-liquid partitioning with petroleum ether and dichloromethane solvents. C6 provides improved cleanup required for data analysis and recovery on polar and nonpolar residues. Lastly, mass spectrometry reveals the structures of all the pesticides present in the food in question (analyte). The data from mass spectrometry will be cross-referenced with pesticide tolerance levels set forth by the U. S. Environmental Protection Agency (EPA) to determine whether or not a particular food, local or imported, is safe to consume by the American people. Application of this method in case studies will be presented.

CHED 226

Detection of Salmonella in foods via microbiological methods

Irene Sun1, [email protected], Angela Lara2, Paris D. Svoronos1. (1) Chemistry, Queensborough Community College, Bayside, New York, United States (2) Food and Drugs Administration, NE Region, Jamaica, NY, Jamaica, New York, United States

The ability of microorganisms to grow and reproduce in foods has been a growing concern for many years. Microorganisms may cause spoilage or chemical changes in the food and injury or death to the individual. The Food and Drug Administration (FDA) sets scientific standards on testing foods for various contaminants. The Microbiological methods listed in the Bacteriological Analytical Manual (BAM) are examples of analytical methods used for the detection of pathogens (bacterial, viral, parasitic, yeast and mold) and microbial toxins. Salmonella will be the focus of this presentation. Media production, food preparation, isolation and identification of Salmonella comprise the microbiological methods that will be discussed in detail.

CHED 227

Treatment of wastewater samples at the New York City-Department of Environmental Protection (NYC-DEP)

Jean Hwang1, [email protected], Faye Jacques2, Panayiotis Meleties3, Paris D. Svoronos1. (1) Chemistry, Queensborough Community College, Bayside, New York, United States (2) New York City-Division of Environmental

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Protection, Ward's Island, New York, United States (3) Office of the Provost, York College, Jamaica, New York, United States

The New York City Department of Environmental Protection (NYC-DEP) is responsible for cleaning the wastewater and protecting the environment in New York City. The Newtown Creek wastewater treatment plant in Brooklyn tests the treated wastewater from all 14 plants every day via its chemistry and microbiology research laboratories. When samples arrive in the lab they are separated into four different groups – acidified, non-acidified, processed solids and total solids. After they are tested for their pH value samples are composited according to an established flow sheet. Details of this procedure and examples of cases encountered daily will be described. The difference in the processing of Total Suspended Solids (TSS) and Total Solids (TS) using primary and secondary digesters that reduce the degree of pathogens during treatment will also be highlighted.

CHED 228

Conversion of biomass to value added chemicals

Alexander W. Bassett1, Jason D. Smith2, Justin Seay2, [email protected], Timothy W. Gaus2, [email protected], Heena Patel2, [email protected], Joseph F. Stanzione1, Amos M. Mugweru2, Kandalam V. Ramanujachary2, Subash C. Jonnalagadda2. (1) Chemical Engineering, Rowan University, Glassboro, New Jersey, United States (2) Chemistry and Biochemistry, Rowan University, Glassboro, New Jersey, United States

The ever increasing energy demand worldwide is causing rapid depletion of fossil fuels, and it has become imperative to seek alternate sources of renewable energy. Biomass offers a cheap, renewable, and abundant alternative for the production of value-added chemicals and fuels. Furan-2,5-dicarboxylic acid (FDCA), one of the most promising chemicals derived from biomass is found to be an ideal replacement for terephthalic acid, which is used in polymer industry for manufacturing polyethylene terephthalate (PET). Similarly, 5-hydroxymethyl-2-furfural (HMF) has also been considered an important and renewable platform chemical derived from biomass. We have previously identified methods for the facile conversion of biomass-derived sugars to HMF, and FDCA and for potential use as bio-based polymers. The presentation will focus on our recent investigations involving the the conversion of biomass derived chemicals into polymeric materials employing reactions such as Baylis-Hillman reaction and reductive amination.

CHED 229

Epoxidized soybean oil polymers

Yevgeniy Vvedenskiy , [email protected], Homar S. Barcena. Physical Sciences, Kingsborough Community College, New York, New York, United States

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Polymers and polymer composites derived from plants are greener alternatives to petroleum-based plastics because of their potential as renewable, biodegradable, and carbon-neutral products. Epoxidized soybean oil (ESO) is a commercially successful plant-derived material that is used as plasticizers, in UV cure applications, in pigment dispersions, and as fuel additives. We synthesized epoxidized soybean oil and co-polymerized the resulting product to develop high-molecular weight polymers in an effort to explore the green chemistry of polymers.

CHED 230

Empirical model of polymer electrolyte membrane fuel cells (PEMFC) using Vulcan/Pt/Ce(III) catalysts in ethanol

Leilani M. Lotti Diaz, [email protected], Yaileen M. Garcia Herrera, [email protected], Krystel Ocasio Norat , [email protected], Rolando Guzmán Blas. Natural Sciences, Universidad del Sagrado Corazón, Ponce, Puerto Rico, United States

The technology of fuel cells has received much attention in recent years due to its high efficiency and low emissions of pollutants. Simulations and models are helpful for developers to improve the design of fuel cells as well as reduce costs, optimize and make them more efficient. A good model should predict the performance of fuel cells in a wide range of operating conditions. Some important parameters to include in a fuel cell model are the cell temperature, fuel temperature, temperature of the oxidant, the pressure of fuel or oxidant, voltage and electric current of the cell, and the fraction weight of each reagent. It is possible to develop models and simulations using Scilab program. Though there are different types of fuel cells, our studies focus on a Polymer Exchange Membrane Fuel Cell (PEMFC) that contains a Vulcan-Pt-Ce(III) doped catalyst that has demonstrated optimization of catalyst material and uses ethanol as fuel for the anode and air or oxygen for the cathode. The fuel cell models obtained will be compared to experimental data and used as an analytical tool to describe the characteristics of voltage vs. electricity in this particular cell.

CHED 231

Development of a greener synthesis of diarylisoxazoles

Gabriella Faux1, [email protected], Kerry McCord1, [email protected], Bridgitt Leon1, [email protected], Alysha E. Moretti1,2, YiTing Lin1, Amber Char1, James Proulx1, Grant Shaffer1, Sam Tatum1, Caitlin Kugelman-Lester1, Tyler Rank1, Joseph Loftus1, Shane Murray1, Loyd Bastin1. (1) Chemistry, Widener University , Chester, Pennsylvania, United States (2) Chemistry and Chemical Biology, Rutgers University, Feasterville Trevose, Pennsylvania, United States

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Isoxazoles have a wide variety of uses in the pharmaceutical industry. They are used as antiepileptic, anticonvulsants, and anti-inflammatory medications. The traditional isoxazole synthesis generated large amounts of waste and contained many hazardous reagents. We have developed a green synthesis for 3,5-diarylisoxazoles that efficiently produces a large variety of diarylisoxazole derivatives. The first step in the greener synthesis, an aldol condensation, converts the substituted benzaldehyde and acetophenone to the corresponding chalcone. Next, the chalcone is brominated to produce the 2,3-dibromochalcone. Lastly, the dibromochalcone is converted to an isoxazole. We have successfully produced isoxazole derivatives containing bromine, chlorine, nitro, methyl, methoxy, ethyl, ethoxy, and phenyl groups in a variety of locations on the isoxazole. All products were analyzed by NMR spectroscopy.

CHED 232

Understanding DNA interaction and biological properties of Ru(II)Pt(II) bimetallic complexes

Denali H. Davis, [email protected], Ty A. Sampsell, Avijita Jain. Chemistry, Indiana University of Pennsylvania, Indiana, Pennsylvania, United States

Mixed metal bimetallic complexes containing ruthenium based light absorbers and a cisplatin moiety represent an emerging class of bioactive molecules that display multifunctional interactions with DNA. Herein, we will discuss DNA interaction, and biological properties of a series of Ru(II)Pt(II) bimetallic complexes with general formula, [Ru(biq)2(BL)PtCl2]

2+ (biq = 2,2'-biquinoline, BL = bridging ligand), consisting of a sterically strained Ru(II)-based light absorber coupled to a cisplatin moiety. Preliminary cytotoxicity studies of designed metal complexes on planarians will be presented.

CHED 233

Intercalation chemistry of iron-based superconductors

Hector Vivanco, [email protected], Xiuquan Zhou, Efrain E. Rodriguez. Chemistry and Biochemistry, University of Maryland, College Park, Maryland, United States

Superconductivity is the phenomenon whereby the electrical resistivity of a material goes to zero. In addition to their potential to revolutionize energy efficiency for electrical transport, these materials are also used to produce large and stable magnetic fields in instruments such as Magnetic Resonant Imaging machines. Recently in 2008, iron-based superconductors were discovered. Iron-based superconductors are composed 2D motif, which allows for easy structure manipulation and subsequent fine tuning of their physical properties. We present the hydrothermal de-intercalation of KxFe2-yS2 for the preparation of FeS single crystals, and we also show the phase diagram of the (LiOH)FeS single crystal system. Both systems represent new simple sulfides as iron-based superconductors. Very recently, the basic binary system, tetragonal-FeS, was reported to be a superconductor up to a critical temperature (Tc) of 5 K. However, the

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study of the physical properties of tetragonal-FeS is still hindered by the lack of high quality single crystal samples. Our goal is to grow single crystals of tetragonal-FeS through novel hydrothermal de-intercalation of KxFe2-yS2, which is a gateway to many layered systems. For example, the LiOH intercalated FeS single crystal can be readily prepared via in situ hydrothermal ion exchange with the KxFe2-yS2 crystal. The LiOHFeS single crystal adopts a primitive tetragonal structure similar to the previously reported selenide analogue. Previously, the polycrystalline form of LiOHFeS was reported to be Pauli paramagnetic, while our new LiOHFeS single crystals were found to be superconducting with Tc between 1.6 K and 7 K. With the results of the new single crystal, it is evident that the Tc for the FeS system can be increased with intercalation. Further studies on other intercalates in the FeS system will be carried out in the future.

CHED 234

Syntheses, characterization, and oxygen reactivity of three coordinate SNS copper(I) pincer complexes

John R. Miecznikowski, Michael Smith, [email protected], Margaret Siu, Nicholas A. Bernier. Chemistry and Biochemistry, Fairfield University, Fairfield, Connecticut, United States

Recently, we have developed and synthesized a series of tridentate pincer ligands, each possessing two sulfur- and one nitrogen-donor functionalities (SNS), based on bis-imidazole or bis-triazole precursors. The tridentate SNS ligands incorporate thione-substituted imidazole or triazole functionalities. We have prepared somewhat rigid ligand systems through the use of 2,6-dibromopyridine as a ligand precursor. In addition, we have prepared more flexible ligand systems by employing the starting material 2,6-(dibromomethyl)pyridine to introduce a methylene linker into the pincer

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ligand. We have metallated these ligand precursors to form copper(I) and (II) complexes (figure 1, 1-3 a-c). The complexes have already been synthesized and thoroughly characterized. The geometry of some copper(I) complexes allows for studies on the oxygen transfer activity. The copper complexes will be tested for reactivity toward hydrogen peroxide. A detailed description of the syntheses, characterization (X-ray diffraction, electrochemistry, UV-Vis), and reactivity of the SNS copper complexes toward an oxygen atom donor will be presented.

Figure 1: SNS Cu(II) and Cu(I) Pincer Complexes

CHED 235

Use of a bis(indenyl)zirconium(II) complex as a coactivator organometallic to access reactive, low valent transition metals

Christopher A. Bradley, Zachary Call, [email protected]. Science, Mount St. Mary's University, Emmitsburg, Maryland, United States

To activate and functionalize strong C-H bonds, a highly reactive metal catalyst is needed to perform the desired transformation. These catalysts are primarily based on precious metals in Group 9 due to their high activity. There is a focus within chemistry to make industrial scale processes more sustainable and green. To do this, the reagents and process that are chosen must be less dangerous, more renewable and utilize more abundant metals. By using metals such as cobalt instead of platinum in C-H activation, it can cut down specifically on the expense and can expand the long-term viability of these reactions. Our group works to develop new strategies to access reactive, low oxidation state cobalt species which can serve as active catalysts in a variety of carbon-hydrogen bond activation reactions for this purpose, to ultimately increase the sustainability of commercial processes. We have synthesized the desired bis(indenyl) zirconium(II) complex as well as conducted proof of concept experiments with titanium; demonstrating group transfer to the Zr complex is possible. With this project, we will be continuing to use of the bis(indenyl) zirconium(II) complex as a co-catalyst with a commercially available cobalt compound. Zirconium, along with other group 4 metals, serve as a reductant to provide reactive cobalt species that we hope will be capable of acting as a catalyst in the activation and functionalization of carbon-hydrogen bonds.

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Proof of concept studies between cobalt and the Zr(II) complexes will also be presented.

CHED 236

Reactions of first-row metal(II) triflates with 3,6-bis(2-pyridyl)-1,2,4,5-tetrazine

Jillian Manikoff, [email protected], Matthew Cranswick. Chemistry, Colorado State University - Pueblo, Pueblo, Colorado, United States

Few studies have investigated the reactivity of metal-tetrazine complexes towards small molecule activation. We are investigating the formation of bimetallic complexes in which at least one ligand is derived from the non-innocent ligand 3,6-bis(2-pyridyl)-1,2,4,5-tetrazine (bptz). Our initial studies have focused on the reactions of M(OTf)2 (where M = Mn, Fe, and Co; OTf– = CF3SO3

–) with bptz in acetonitrile. The isolated products from these reactions have been analyzed using standard characterization techniques.

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CHED 237

Synthesis, characterization, and catalytic behavior of mono- and bimetallic ruthenium(II) complexes supported by pyridine-functionalized N-Heterocyclic carbene ligands

Joshua Zgrabik, [email protected], Gregory J. Domski. Chemistry, Augustana College, Rock Island, Illinois, United States

We have prepared and characterized several previously unreported ruthenium(II) complexes supported by pyridine-functionalized N-heterocyclic carbene ligands. These complexes have shown potential as transfer hydrogenation catalysts.

CHED 238

Naphthyridine-based dicarboxamide ligand for the synthesis of dicopper complexes that model metalloenzyme intermediates

Janaya Sachs1, [email protected], Nicole L. Gagnon2, William B. Tolman2. (1) Chemistry, Eastern Mennonite University, Dillsburg, Pennsylvania, United States (2) Chemistry, University of Minnesota, Minneapolis, Minnesota, United States

Copper oxygen complexes are postulated to be capable of oxidizing strong C-H bonds, including in enzymes. For example, particulate methane monooxygenase (pMMO) is proposed to feature a dicopper active site with a short Cu-Cu distance (~2.7 Å) that activates oxygen to yield a reactive intermediate capable of attacking the strong C-H bond of methane. We aim to design small molecule complexes as models of the proposed pMMO active site intermediate. Our strategy involves using a new ligand comprised of a 1,8-naphthyridine unit and two carboxamide moieties with sterically bulky aryl substituents designed to hold two copper ions in close proximity and stabilize novel targeted copper-oxygen species with multiple oxidation states. We report the successful synthesis of this new ligand, the formulation of which is supported by various spectroscopic data. Initial generation of copper complexes will also be described.

CHED 239

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Substituent effects on the photochemistry and DNA interaction properties of Ru(II)Pt(II) based polypyridyl complexes

Alexis E. Hagelgans, [email protected], Ty A. Sampsell, Avijita Jain. Chemistry, Indiana University of Pennsylvania, Indiana, Pennsylvania, United States

Ru(II)Pt(II) bimetallic complexes consisting of a ruthenium based chromophore coupled to a cisplatin moiety have been shown to display multifunctional interactions with DNA. Herein, we will discuss the impact of position of the methyl group on bipyridine ligand on photophysical and redox properties of Ru(II)Pt(II) bimetallic complexes. Two Ru(II)Pt(II) based metal complexes, [Ru(4-Mebpy)2dppPtCl2](PF6)2 and [Ru(6-Mebpy)2dppPtCl2](PF6)2, were synthesized and characterized (dpp =2 3-bis(2-pyridyl)pyrazine and 4-Mebpy = 4'-methyl-2,2' bipyridine, 6-Mebpy = 6'-methyl-2,2' bipyridine). Photochemical, electrochemical, and DNA interaction properties of designed metal complexes will be discussed.

CHED 240

Isomers and interconversions at eight-coordinate rhenium(V) polyhydride centers

Alexis Scorzelli, [email protected], Brian Macalush, [email protected], Georga Torres, [email protected], Gregory A. Moehring. Chemistry and Physics, Monmouth University, West Long Branch, New Jersey, United States

A series of eight-coordinate rhenium(V) complexes have been prepared and studied by variable temperature NMR spectroscopy in order to better understand both the appearance of isomers for such complexes and the mechanism of the interconversion between such isomers. Previously, X-ray diffraction analysis has found cis and trans isomers for rhenium(V) cations of the formula [Re(mhp)2H2(PPh3)2]

+ (where mhp = the anion of 2,6-methylhydroxypyridine) and low temperature NMR spectroscopy has demonstrated the presence of isomers for rhenium(V) complexes of the form ReH5(PPh3)2L (where L = an unsymmetrically substituted aromatic amine ligand such as 2-aminopyridine or the secondary amine NHMeEt). In this study, isomers of the form ReH4(E-N)(PPh3)2 (where E-N represents a monoanionic chelating ligand that binds through both a nitrogen center and another atom such as C or O) are reported. In the course of our studies we have examined the occurrence and interconversion of isomers in a variety of eight-coordinate rhenium systems that involve the presence of absence of a chelating ligand, the presence or absence of a chiral center, and the presence or absence of a plane of symmetry for the chelating ligand as well as the interconversion of phosphorous centers in a complex such as ReH5(PPh3)3 which does not present isomers. Determinations of the free energy of activation for interconversions of isomers find values in the neighborhood of 10 kcal/mol. Determinations of enthalpies of activation and entropies of activation indicate that enthalpy is the substantial contributor to the free energy of activation. All of our observations such as the thermodynamic parameters, the equivalence of inequivalent phosphorous centers in higher temperature

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NMR spectra, and the presence or absence of isomers for specific stroichiometries corresponds to a single mechanism for the fluxional rearrangement of all bulky ligands at eight-coordinate rhenium(V) centers. The rearrangement corresponds to rotation of a set of four inner sphere ligand atoms bound to one side of the metal center with respect to the four ligand atoms bound to the opposite side of the metal center. Evidence in support of this mechanism for isomer interconversion is presented.

CHED 241

Systematic synthesis of a linked triosmium cluster system via 1,5-pentanediol bridging ligands

Robert Sommerhalter, [email protected], Mary-Ann Pearsall. Chemistry, Drew University, Madison, New Jersey, United States

With the goal of developing systematic syntheses of linked triosmium carbonyl clusters, we report the substitution reactions of the dibridged cluster Os3(CO)10(µ

2-OEt)2 with the bifunctional ligand 1,5-pentanediol. Reaction of Os3(CO)10(µ

2-OEt)2 with 1,5-pentanediol affords the cluster Os3(CO)10(µ

2-O(CH2)5OH)2 as the major product. Over extended reaction periods, quantitative conversion to the cluster H4Os4(CO)12 is observed. Linking of two triosmium carbonyl clusters via the 1,5-pentanediol bridging ligands has been achieved in the reaction of Os3(CO)10(µ

2-O(CH2)5OH)2 with one molar equivalent of Os3(CO)10(µ

2-OEt)2. A secondary product of this reaction has been characterized spectroscopically and is believed to be an intermediate in the formation of H4Os4(CO)12.

CHED 242

Reactions of amides with dibridged triosmium carbonyl clusters

Katherine E. Marak, [email protected], Mary-Ann Pearsall. Chemistry, Drew University, Madison, New Jersey, United States

The reactions of the dibridged triosmium cluster, Os3(CO)10 (µ2-OEt)2, with amides are

presented. The reaction with acetamide (CH3CONH2) is found to be analogous to the reaction of the cluster with carboxylic acids, which yield a diosmium complex, but the possibility of isomers is introduced. Spectroscopic data indicate that both isomers of Os2(CO)6(CH3CONH)2 are observed.

CHED 243

Synthesis and characterization of vanadium(V) complexes from a novel Schiff base, (E)-N'-(5-((Z)-(4-fluorophenyl)diazenyl)-2-hydroxybenzylidene)benzohydrazide

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Jaya Chhabra, [email protected], Deondra T. Brown, Raj K. Gurung, Michael J. Celestine , Alvin Holder. Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia, United States

Since 1899, vanadium-containing compounds have been utilized as insulin-like agents in alleviating the symptoms of diabetes. More recently, many researchers, including our research group, have been designing and synthesizing vanadium-containing compounds to be used as chemotherapeutic agents. As such, we have continued our efforts, by synthesizing a novel ligand, (E)-N'-(5-((Z)-(4-fluorophenyl)diazenyl)-2-hydroxybenzylidene)benzohydrazide (F-azo- salhyph), and then used it to synthesize and characterize two novel vanadium(V) complexes. The complexes were characterized by elemental analysis, UV-visible, 1H, 13C, and 51V NMR, FTIR spectroscopies, as well as electrochemical studies. Definitive details including stability and speciation studies in water and non-aqueous solvents will also be presented.

CHED 244

Synthesis and characterization of vanadium(IV) complexes from a novel Schiff base, (E)-N'-(5-((Z)-(4-fluorophenyl)diazenyl)-2-hydroxybenzylidene)benzohydrazide

Deondra T. Brown, [email protected], Jaya Chhabra, Raj K. Gurung, Michael J. Celestine , Alvin Holder. Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia, United States

Since 1899, vanadium-containing compounds have been utilized as insulin-like agents in alleviating the symptoms of diabetes, but more recently, many researchers, including our research group, have been designing and synthesizing vanadium-containing compounds to be used as chemotherapeutic agents. We have synthesized a novel ligand, (E)-N'-(5-((Z)-(4-fluorophenyl)diazenyl)-2-hydroxybenzylidene)benzohydrazide (F-azo- salhyph), and then used it to synthesize and characterize two novel vanadium(IV) complexes. The complexes were characterized by elemental analysis, UV-visible, 1H and 13C NMR, EPR, and FTIR spectroscopies, as well as electrochemical studies. Definitive details including stability and speciation studies in water and non-aqueous solvents will also be presented.

CHED 245

Synthesis, characterization, and catalytic behavior of mono- and bimetallic iridium(III) complexes supported by pyridine-functionalized N-heterocyclic carbene ligands

Isaac Smith, [email protected], Gregory J. Domski. Chemistry, Augustana College, Rock Island, Illinois, United States

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We have prepared and characterized several previously unreported iridium(III) complexes supported by pyridine-functionalized N-heterocyclic carbene ligands. These complexes have shown catalytic potential as transfer hydrogenation catalysts.

CHED 246

Synthesis and characterization of [RhIII(NNN)(NN)L]n+

Peter Nunez, [email protected], Daniel Amarante. Division of Natural Sciences, College of Mount Saint Vincent, Riverdale, New York, United States

Several complexes of the general formula, [RhIII(NNN)(NN)Cl]2+, have been synthesized (where NNN = 2,2':6',2"–terpyridine, 4'–chloro–2,2':6',2"–terpyridine, 4'–(4–chlorophenyl)–2,2':6',2"–terpyridine, 4'–methyl–2,2':6',2"–terpyridine and NN = 2,2'–bipyridine, 1,10'–phenanthroline, 4,4'–dimethyl–2,2'–bipyridine, 3,4,7,8–tetramethyl–1,10'–phenanthroline and 4,4'–dimethoxy–2,2'–bipyridine). These complexes were synthesized using a modified literature procedure. All complexes were precipitated as the PF6

– salt, without any purification, with yields ranging from 60% to 90%. Complexes were characterized using NMR and UV–Vis. Crystallization, for X–ray diffraction, of these products are currently being investigated. Continuing trials to convert the chloride complex to the triflate have shown interesting results, however with low yields. Optimization of these products are currently being performed. The complex of [RhIII(NNN)(NN)(OTf)]2+ will be synthesized with pyPorH2 (pyridylporphyrin) and its analogs to study their photochemical and photophysical properties.

CHED 247

Synthesis of a chloride chemosensor by ligand structure manipulation

Nicholas Brocious, [email protected], Jessica M. Fautch. Physical Sciences, York College of Pennsylvania, York, Pennsylvania, United States

Chloride is a common ion found in many aqueous media solutions, but there have been difficulties using a luminescent sensor for a 1:1 quantification. The goal of this research is to find a ligand structure to create a nickel(II) pincer complex that is a chemosensor for chloride in solution. Using past research on the topic, and others similar to it, including research about platinum(II) pincer complexes, the nickel(II) pincer complex will be synthesized and categorized using IR, 13C and 1H NMR spectroscopies.

CHED 248

Effects of alkyl group and NHC ligand variation with ruthenium-based olefin metathesis catalysts bearing chelating ortho-alkoxy benzylidenes

Shaoxiong Luo1, [email protected], Keary Engle1, Peng Liu2,3, Xiaofei Dong2, Buck L. Taylor2, Michael K. Takase1, Kendall N. Houk2, Robert H. Grubbs1. (1)

Page 140: CHED Abstracts

Chemistry, California Institute of Technology, Pasadena, California, United States (2) Chemistry and Biochemistry, University of California Los Angeles, Los Angeles, California, United States (3) Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania, United States

A series of second-generation ruthenium olefin metathesis catalysts was investigated using a combination of reaction kinetics, X-ray crystallography, NMR spectroscopy, and DFT calculations in order to determine the relationship between the structure of the chelating ortho-alkoxybenzylidene and the observed initiation rate. Included in this series were twenty new catalysts containing an array of ortho-alkoxy benzylidenes and NHC ligands. The initiation rates of this series of catalysts were determined using a UV/Vis assay. All new catalysts were observed to be faster-initiating than the corresponding isopropoxy control, and the dicyclohexylmethyl catalyst was found to be among the fastest-initiating Hoveyda-type catalysts reported to date. Analysis of the X-ray structures and computed energy-minimized structures of these catalysts revealed no correlation between Ru–O bond length and Ru–O bond strength. On the other hand, the initiation rate was found to correlate strongly with the computed Ru–O bond strength. This latter finding enables both rationalization and prediction of catalyst initiation through calculation of a single thermodynamic parameter, in which no assumptions about mechanism of the initiation step are made.

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CHED 249

Synthesis of substituted silicone nanospheres and characterization by X-ray fluorescence (XRF) spectroscopy

Meagan Suchewski, [email protected], Annie Kayser, [email protected], Christopher A. Bradley. Science, Mount St. Mary's University, Emmitsburg, Maryland, United States

Nanoparticles have demonstrated many valuable properties relative to other small molecules and solid surfaces. For example, they have a high surface area, which allows them to increase the number of potential active sites for reactions. We are specifically focusing on the synthesis of silicone nanospheres, which can be accessed by condensation polymerization of alkyl trimethoxymethylsilanes. The value of these materials stem from their simple synthesis at ambient temperature from commercial reagents and the ease with which they can be purified by filtration. This synthetic strategy allows installation of a variety of functional groups into the nanosphere, including heavy atoms, like sulfur and phosphorous. The nanospheres are characterized using several methods, including NMR spectroscopy, dynamic light scattering and transmission electron microscopy (TEM). We have also used a new method, X-ray fluorescence (XRF) spectroscopy, which will provide elemental distributions for the materials. With the functionalized nanoparticles in hand, we hope to graft metals onto the surfaces, characterize them using XRF, and attempt to use these supported materials as catalysts in organic trasnformations.

CHED 250

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Mechanism of the oxidation of a cobaloxime by sodium bromate in aqueous solution

Brianne S. Nunez, [email protected], Michael J. Celestine , Alvin Holder. Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia, United States

An investigation of the oxidation of [Co(dmgBF2)2(OH2)2] (where dmgBF2 = difluoroboryldimethylglyoximato) by sodium bromate, NaBrO3, was carried out by stopped-flow spectrophotometry at 450 nm, temperature of 25.0 °C, and over the range of 1.00 mM ≤ [HCl] ≤ 11.00 mM, with a constant ionic strength of 0.60 M (NaCl). From the obtained data, a mechanism for the reaction was proposed. From the mechanism the following rate expression was derived: k = kobs/[NaBrO3] = a[H+] + b[H+]2 (where a = k1 and b = k-1/k2). The values for a and b were calculated as 3.4 x 102 M-2 s-1 and 9.2 x 104 M, respectively, at 25.0 °C. When the concentration of NaBrO3 was varied, two rate constants were observed, viz., k3 = 4.6 x 10-4 s-1, which corresponded to either a reaction pathway independent of the NaBrO3 concentration or the reverse process in an equilibrium process, and k4 = 2.9 x 10-3 M-1 s-1, which was dependent on the concentration of the oxidant. The mechanism of the oxidation of [Co(dmgBF2)2(OH2)2] by NaBrO3 will be discussed in light of the kinetics data.

CHED 251

Synthesis, characterizations, and DNA-binding and cytotoxicity studies of tricarbonylrhenium(I)-diimine complexes of ibuprofen

Sabreea Parnell1, [email protected], Saroj Pramanik3, Santosh K. Mandal1. (1) Chemistry, Morgan State University, Baltimore, Maryland, United States (3) Biology, Morgan State University, Baltimore, Maryland, United States

Numerous transition-metal complexes of nonsteroidal anti-inflammatory drugs (NSAIDs) are known. However, examples of organometallic complexes of NSAIDs are scarce. Using a variety of NSAIDs, our lab has synthesized a wide range of organorhenium complexes of NSAIDs. Recently, we have synthesized a series of tricarbonylrhenium(I)-diimine complexes of ibuprofen from the reactions of the corresponding pentylcarbonato complexes with stoichiometric amount of ibuprofen. The ibuprofenate complexes have been characterized through FT-IR spectrophotometry and NMR spectroscopy. The UV-titrations of the ibuprofenates with CT-DNA suggest that many of the ibuprofenates bind to DNA through intercalation. The cytotoxicity studies of the ibuprofenates against U-937 lymphoma cells confirm that the ibuprofenates are moderately cytotoxic.

CHED 252

Synthesis, characterizations, and DNA-binding and cytotoxicity studies of tricarbonylrhenium(I)-diimine complexes with mefenamic acid

Page 143: CHED Abstracts

Tiara Hinton1, [email protected], Saroj Pramanik3, Santosh K. Mandal1. (1) Chemistry, Morgan State University, Baltimore, Maryland, United States (3) Biology, Morgan State University, Baltimore, Maryland, United States

Transition-metal complexes of non-steroidal antiinflammatory drugs (NSAIDs) are of importance because they possess intersting biological properties. Our lab is engaged in the synthesis of organorhenium complexes of NSAIDs. Recently we have found that the reactions of tricarbonylrhenium(I)-diimine pentylcarbonato complexes with stoichiometric amount of flufenamic acid afford the corresponding flufenamato complexes quantitatively. We have characterized them spectroscopically and, in many cases, crystallographically. The UV-titrations of the flufenamato complexes with CT-DNA suggest that some of these complexes bind to DNA intercalatively. The IC-50 values of these complexes against U-937 lymphoma cells are greater than 2 μM which is far less than the IC-50 value of cisplatin against lymphoma cells.

CHED 253

Mixed sulphadoxine-aspirin metal complexes: Synthesis and antimicrobial studies

Joshua A. Obaleye1, Stephen T. Adekunle1, [email protected], Abdullahi O. Rajee1, Mariam O. Abbass1, Funto V. Adewumi3. (1) Chemistry, University of Ilorin, Ilorin, Kwara State, Nigeria (3) Industrial Chemistry, University of Ilorin, Ilorin, Kwara State, Nigeria

Malaria is an important cause of death and illness in children and adults in tropical countries. Malaria is a global public health problem, affecting about 400 million people worldwide and causing about 3 million deaths annually, mainly among children under five years old. The increasing resistance to currently available anti-malarial drugs have stimulated new efforts regarding the development of new chemotherapeutic drugs. Metal complexes have shown significant increase in inhibition activity when compared to pure drugs. The study of metal complexes is of special interest, owing to their enhanced biological activities. As part of our ongoing research into more effective drugs, mixed ligand-metal complexes of sulphadoxine-aspirin have been prepared. The products were characterized using elemental analysis, IR, UV/Visible spectroscopies and some physico-chemical studies. The electronic transitions observed also revealed the formation of new complexes of the ligands. In-vivo evaluation of the antimicrobial activity showed that, when compared to the parent compound, metal complex and the ligand showed greater activity against the following microorganisms: Escherichia coli, Klebsiella pneumonia, Staphylococcus aureus, Bacillus substilis, and Pseudomonas aereginosa. Both sulphadoxine and aspirin moieties were found to be bidentate in coordination to the central metal ion via the lone electron pairs located on the oxygen and nitrogen atoms present in their molecules.

CHED 254

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Synthesis and characterization of an iron(III) amine triphenolate coordination complex

Kerry C. Casey, [email protected], Lauren A. Steigen, Ursula J. Williams. Chemistry, Juniata College, State College, Pennsylvania, United States

Tripodal iron coordination compounds have been studied as model complexes for biological and industrial catalytic processes, including small molecule activation reactions. As part of a larger study considering the impact of ligand identity on the redox properties of iron coordination complexes, we set out to synthesize iron coordination complexes in an amine triphenolate ligand environment. We will describe the synthesis and characterization of this ligand and its coordination to iron. We are pursuing characterization of the resulting complexes using X-ray crystallography and cyclic voltammetry.

CHED 255

Photophysical and chiroptical properties of europium(III) complexes with tetracycline derivatives

Mizuki Johnson, [email protected], Adrian Riives, Gilles Muller. Chemistry, San Jose State University, San Jose, California, United States

One of the nature's fundamentals is that structure determines function. It is natural for biological molecules (biomolecules) with active functions to be dependent on structural characteristics, such as chirality and anisotropy. Therefore, one field of research is to develop robust, sensitive, specific techniques capable of determining biomolecules’ proper structural characteristics and, to a greater extent, be able to detect distinct molecules. In recent years, luminescent lanthanides have been used for specialized chemical application in designing non-invasive bioprobes. The trivalent Eu(III) ion is one of the most emissive of all lanthanide ions due to its long-lived 5D0 excited state. The goal of this project is to understand how metal chelation, pH, and solvents contribute to the ability of tetracycline (TC) derivatives to chelate to Eu(III) and be used as a luminescent probe. Steady-state and time-resolved luminescence spectroscopic measurements as well as circularly polarized luminescence spectroscopy were used to determine the stability of each Eu:TC derivative species over a range of pH.

CHED 256

Synthesis and characterization of new rhodium alkene complexes containing hemilabile P-O ligands

Christian J. Adams, [email protected], Joseph T. Medina, [email protected], Giovanni A. Ramirez, Armando A. Urbina, Christine Hahn. Chemistry, Texas A&M University - Kingsville, Kingsville, Texas, United States

Page 145: CHED Abstracts

The development of new rhodium catalysts for alkene and alkyne functionalization reactions (e.g., hydroformylation, alkyne dimerization, hydroarylation) is the subject of current research. In order to explore new structures and reactivity, two types of hemilabile ligands were prepared containing both phosphorus and oxygen donor atoms. The first type of ligands, bisphosphine monoxide ligands, were synthesized by selective oxidation using palladium catalyst. The second type of ligand being studied was a phosphinoketone. The new rhodium alkene complexes were prepared using [RhCl(alkene)2]2 as precursor complex. After halide abstraction by silver or thallium salts in the presence of another donor ligand, the resulting [Rh(P-O)(L)(alkene)]+ complexes (L = PPh3, NR3) were characterized by 1H, 13C, and 31P NMR and IR spectroscopies and crystal structure analysis.

CHED 257

Reduction of carbon disulfide at rhenium polyhydride centers

Devyn J. Streisel, [email protected], Andrew L. Petrou, [email protected], Gregory A. Moehring. Chemistry and Physics, Monmouth University, West Long Branch, New Jersey, United States

Carbon disulfide is an effective solvent for low temperature studies of rhenium(V) pentahydride complexes supported by two triphenylphosphine ligands and an aromatic amine ligand but it leads to decomposition of analogous compounds supported by primary amines rather than by aromatic amines. The only previous report of a reaction between carbon disulfide and a rhenium polyhydride complex involved a rhenium pentahydride center supported by a tridentate tertiary phosphine ligand and resulted in insertion of a CS bond into an Re-H bond. In this study, carbon disulfide reduced further to a methanedithiolate ligand when reacted with the complex ReH5(PPh3)2(NH2CH2CH2NH2). The new reactant, ReH5(PPh3)2(NH2CH2CH2NH2), contains a dangling amine group which changes into a bound group in the final product. The NMR properties of the product, Re(CH2S2)H(PPh3)2(η

2-NH2CH2CH2NH2), are reported. Reactions between other rhenium polyhydride complexes and carbon disulfide were also explored and those results are reported as well.

CHED 258

Effect of bridging ligand conjugation on bimetallic asymmetric ruthenium(II) complexes and their DNA interactions

Jenally Montalvo1, [email protected], Michael LaCorte1, [email protected], Matthew T. Mongelli2, [email protected], Amy Abdulkarim1, Katherine Thomas1. (1) Chemistry, Kean University, Union, New Jersey, United States (2) Chemistry, Kean University, Lyndhurst, New Jersey, United States

Complexes of the form, [(bpy)2Ru(BL)Ru(Cl)(tpy)]3+,where bpy is the bidentate terminal ligand 2,2’-bipyridine, tpy is the tridentate terminal ligand 2,2’:6’,2”-terpyridine and BL is

Page 146: CHED Abstracts

a bridging ligand (i.e. 2,3-bis(2-pyridyl)pyrazine (dpp), 2,3-di(pyridin-2-yl)-6,7-dihydroquinoxaline (dpq), or 2,3-di(pyridin-2-yl)benzo[g]quinoxaline (dpb)), have been synthesized. These complexes are being investigated for their ability to bind and/or photocleave DNA through visible light photolysis. The synthesis and characterization of the complexes will be presented as well as DNA interaction assays.

CHED 259

Design and synthesis of a macrocyclic non-covalent proteasome inhibitor

Megan A. Rocha, [email protected], Robert S. Dorn, [email protected], Marion G. Gotz. Chemistry, Whitman College, Walla Walla, Washington, United States

The proteasome has in recent years become an important target for the treatment of multiple myeloma. The fungal macrocyclic peptide metabolite TMC-95A is a potent and selective inhibitor of the 26S proteasome. Due to its synthetic complexity, analogues that have similar potency and selectivity but are synthetically more accessible have been pursued. This research explores the synthesis of a macrocyclic TMC-95A analogue that aims to inhibit the proteasome selectively through non-covalent interactions, including hydrogen bonding between the β-extended peptide backbone and the proteasome’s active sites. Previously studied TMC-95A mimics have replaced the synthetically difficult phenyl-oxindole moiety with a diphenyl ether macrocycle. The analogues in this study also contain a biaryl ether linkage, but retain the oxindole heterocycle, as computational modeling has shown that an additional and potentially crucial hydrogen bond is formed between the oxindole and Gly23.

CHED 260

Scaffold-hopping approach to the development of antiseptic cationic amphiphiles

Myles Mitchell1, [email protected], Ryan Allen1, Megan Jennings2, William M. Wuest2, Kevin P. Minbiole1. (1) Chemistry, Villanova University, Villanova, Pennsylvania, United States (2) Chemistry, Temple University, Philadelphia, Pennsylvania, United States

In the world, there is a need for new antiseptic compounds that can lyse bacteria and keep them from reproducing. Current antibacterial compounds have started to become ineffective as more and more strains of bacteria become resistant to them. To counter this trend, our research group has identified a number of bis-, tris-, and tetraamine starting materials for the production of diverse architectures of quaternary ammonium compounds; these resulting amphiphiles show great promise in killing bacteria and eradicating bacterial biofilms. Furthermore, in order to create new compounds that are antimicrobial, yet will decompose before bacteria can become resistant to them, our lab plans to research the synthesis and effectiveness of new antiseptic compounds that can "self-destruct."

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CHED 261

Design, synthesis, and biological evaluation of α-(imidazolylmethyl)cinnamates, α-(imidazolylmethyl)cinnamamides, and p-imidazolyl-α-(imidazolylmethyl)cinnamates

Suman Pathi, Drew Morgan, Alexander Vendola, [email protected], Md. Ashiq Ur Rahman, Alexander Colfer, [email protected], Kent Truong, [email protected], Subash C. Jonnalagadda. Chemistry and Biochemistry, Rowan University, Glassboro, New Jersey, United States

Imidazoles are an important class of heteoaromatic compounds with a ubiquitous ring system that play critical roles in the human body and are present in various biological structures such as as histamine and histidine. The highly electron rich ring structure of imidazoles enables them to bind to various enzymes or receptors and hence they exhibit wide-ranging biological properties ranging from anti-fungal (eg. miconazole, metronidazole), anti-neoplastic (eg, decarbazine, temozolomide), anti-microbial agents (eg. oroidin), etc. Imidazoles are generally soluble in water and other polar solvents, which adds further merit to their development as therapeutics. Based on our interest in heterocyclic chemistry, we undertook the synthesis of highly substituted imidazoles via multicomponent coupling reaction such as Debus-Radziszewski reaction and Baylis-Hillman reaction. The simple reaction conditions coupled with the great diversity imparted by the MCR protocol renders the process further meritorious. Using this protocol, we were able to synthesize a large library of imidazoles with fewer starting materials for carrying out a systematic structure activity relationship assay. We have been able to identify a few potent lead molecules for in vivo preclinical development as anti-cancer agents and this presentation will describe our efforts in this project.

CHED 262

Screening of peptide linked metal chelators: A potential disruptor for amyloid-beta aggregation

Michael Hart, [email protected], Cecilia H. Vollbrecht, Kerry A. Pickin. Chemistry, Centre College, Lexington, Kentucky, United States

Proteins and metals play key roles in infection and disease progression in patients with Alzheimer’s disease. The synthesis of peptide based inhibitors and metal chelators offers a potential alternative for the treatment of the disease. Our research focuses on the screening of these synthesized peptides and peptide linked metal chelators that are designed to disrupt the aggregation of amyloid-beta, the key peptide in the formation of the characteristic neurodegenerative plaque in Alzheimer’s disease. In addition, the peptide chelator complexes are developed to remove and sequester toxic metal ions associated with the aggregates (including Zn2+, Cu2+, and Fe3+). The ability of the compounds to disrupt aggregation is determined by thioflavin-T assays and used to

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evaluate the potential for the compounds to be used in the treatment of Alzheimer’s disease.

CHED 263

Interaction of noncanonical DNA structures with small molecule ligands

Sayed Malawi, [email protected], Deondre Jordan, Delfin Buyco, Liliya A. Yatsunyk. Chemistry and Biochemistry, Swarthmore College, Swarthmore, Pennsylvania, United States

DNA exists in numerous non-canonical conformations in addition to the traditional double helix. One of these conformations is G-quadruplex (GQ), which consists of stacks of guanine quartets formed by four guanines held together by Hoogsteen hydrogen bonds. Sequences with quadruplex forming potential are present in oncogene promoters and human telomeric repeats. As such, they are proposed to play an important role in gene regulation and cancer biology. Small molecules that are capable of binding to or stabilizing GQs can potentially be used as new types of anticancer therapeutics. In this work we have investigated the interactions between small molecule ligands such as porphyrins (NMM, TMPyP4, etc) or extended conjugated systems (RHPS4, Braco-19, etc) and a variety of GQ structures using UV-Vis, CD, and fluorescence titrations, CD melting experiments, and gel electrophoresis. Our data for binding between NMM and various GQ sequences indicates the following binding constants: 0.5 ± 0.2 uM-1 (2 ligand : 1 GQ) for oncogene promoter Bcl-2, 0.16 ± 0.02 uM-1 (1:1) for AcKit1, 1.7 ± 0.9 uM-1 (1:1) for VEGF, 0.3 ± 0.2 uM-1 (1:1) for G4TERT, and 1.7 ± 0.6 uM-1 (2 ligand : 1 GQ) for cMyc. The relatively strong binding constants of NMM to VEGF and cMyc make them good pairings for crystallization. The most promising ligand-GQ pairs are being explored for their ability to produce high quality 3D crystal structures, which will be presented and discussed in our poster.

CHED 264

Comparison of extraction methods for capsaicin

jonathan Will, [email protected], Madisyn Frazee, [email protected], Edmir O. Wade. Chemistry, University of Southern Indiana, Newburgh, Indiana, United States

Chemical compounds found in plants are utilized as the main components in many medications and herbal remedies worldwide. The vast diversity of plant structure and chemical composition makes unstudied plants ideal candidates for medical research. Our investigation will compare the quality of various extraction methods, measuring isolation quality, ease of extraction, cost, and reactive functional group species for the plant compound capsaicin ( (E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide). Known for causing a burning sensation when eaten, capsaicin is a chemical compound in peppers that has been linked to medicinal applications in weight loss,

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cancer cells, and blood pressure. Extraction of this compound will be done via two different solvent separation pathways that remove organic matter from the aqueous layers. Capsaicin will be confirmed as isolated from the mixture through processes of NMR, IR, and Mass Spectrometry. After confirming the isolation of capsaicin, the two methods of solvent separation will be compared. The preferred method will then be used on local and tropical plants with similar compounds to that of capsaicin that have not been studied.

CHED 265

Cytotoxicity and minimal inhibitory concentration evaluation of synthesized benzohydrazide derivatives

Alisha Mason1, [email protected], Sarah Thompson1, [email protected], J. J. Steel2, David L. Dillon3. (1) Colorado State University- Pueblo, Pueblo, Colorado, United States (2) Biology, Colorado State University- Pueblo, Pueblo, Colorado, United States (3) Chemistry, Colorado State University - Pueblo, Pueblo, Colorado, United States

Substituted benzohydrazides, Figure 1, have been shown to have antimicrobial activity and are synthesized via acylation. This interdisciplinary project, involving organic synthesis, microbiological determination of antimicrobial activity, and cytotoxicity, focused on investigation of the effect of various substituents at the N’ and aryl positions on biological activity. The cytotoxicity of these compounds is not well studied. Derivatives 1a,b were previously found to have minimal or slight activity against tested bacteria. Preliminary results of the cytotoxicity have shown certain concentrations of the compounds have high viability for eukaryotic cells. Drug administration was evaluated at different time points using Resazurin/Alamar blue cell viability assays to monitor cytotoxicity in cultured eukaryotic cells with different concentrations. In previous work, antimicrobial activity was examined using Kirby Bauer and measuring zones of inhibition around discs loaded with the compound. The Minimal Inhibitory Concentration is now being evaluated to better understand the concentrations needed to inhibit microbial growth. Exposure times of the compounds were evaluated in an attempt to determine the therapeutic indices for these compounds and investigate their utility as a potential novel treatment option against bacterial pathogens.

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CHED 266

Design and synthesis of some novel 2,4-disubstituted quinazoline derivatives as anticancer agents

Reem f. almutairy, [email protected], Muneerah alsolmi, Afnan Al-Johani, Afnan Mohammed Noor, Ruba Towairqi. pharmacy , KAU, Jeddah, Saudi Arabia

Cancer is considered to be the second major cause of death. Unfortunately, the development of cellular drug resistance and the significant toxicity displayed by most anticancer agents remain the primary barrier for effective chemotherapy. Therefore, searching for newer anticancer agents remains necessary in order to provide novel structural leads with higher selectivity towards tumor cells and minimum side effects. Quinazoline derivatives have received great attention in the field of anticancer agents. They were identified as potent cytotoxic agents, tyrosine kinase inhibitors and DNA-alkylators. On the other hand, pyrazoles are among the pharmacologically chemical scaffolds that have received particular interest as an anticancer agent. In view of the aforementioned facts, and with the aim of finding new structure leads in the field of chemotherapeutic agents, it was of interest to design a new series of 2,4-disubstituted quinazolines. Some of these compounds comprise the pyrazole moiety linked to the 4- position of the quinazoline ring through 3-atom spacer. The objective of forming these hybrids is to investigate the influence of such hybridization on the anticipated biological activity.

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CHED 267

Structure-Resistance Relationships: Interrogating Antiseptic Resistance in Bacteria Using Multicationic Quaternary Ammonium Dyes (multiQACs)

stephanie duggan4, [email protected], Megan Forman3, Madison Fletcher2, Megan Jennings2, Kevin P. Minbiole3, [email protected], William M. Wuest1. (1) Chem Dept, Beury Hall 130, Temple Univ, Philadelphia, Pennsylvania, United States (2) Chemistry, Temple University, Philadelphia, Pennsylvania, United States (3) Chemistry, Villanova University, Villanova, Pennsylvania, United States (4) Villanova University, Villanova, Pennsylvania, United States

Bacterial resistance toward commonly employed biocides is a widespread yet underappreciated problem, one which needs not only a deeper understanding of the mechanisms by which resistance proliferates, but also strategies for mitigation. Bacteria utilize many methods, most notably efflux pumps, to circumvent the lytic capability of quaternary ammonium compounds (QACs). However, currently used QAC antiseptics offer no means to address these modes of resistance. We recognized a polyaromatic structural motif analogous to structures that bind QacR, a negative transcriptional regulator of the efflux pump QacA, and envisioned a series of QACs based on this motif. Starting from commercially available dye scaffolds, we synthesized and evaluated the antimicrobial activity of 52 novel QACs bearing 1-3 quaternary ammonium centers. Striking differences in antimicrobial activity against bacteria bearing QAC resistance genes were observed, with up to a 125-fold increase in MIC for select structures against bacteria known to bear efflux pumps (i.e., MRSA). Trends in structure-resistance relationships are now more apparent. Additionally, we describe a previously overlooked trend regarding the intrinsic resistance of Gram-negative bacterial species.

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CHED 268

Sugar modified pseudouridines as potential anti-viral agents

Joseph Nunnari1, [email protected], Immaculate Sappy2, Amanda C. Bryant-Friedrich3. (1) The University of Toledo, Parma Heights, Ohio, United States (2) Medicinal & Biological Chemistry, The University of Toledo, College of Pharmacy & Pharmaceutical Sciences, Toledo, Ohio, United States (3) University of Toledo, Toledo, Ohio, United States

Advances in the treatment of viral infections have provided new impetus for the pursuit of compounds effective against the polymerases responsible for the synthesis of RNAs and DNAs required for viral replication. We are applying skills in nucleic acid synthesis to the development of methods to modify the sugar moiety of nucleosides and nucleotides of naturally occurring modified ribonucleic acids. We have investigated the synthesis of 2'-C modified pseudouridine, utilizing the introduction of the pseudouridine moiety through a nucleophilic addition to a modified ribonolactone. Several variables were modified to increase the efficiency to obtain these derivatives. These include a) the base protection on pseudouridine, b) the protecting groups on the ribonolactone, c) the reducing agent and subsequent ring closure to give the final modified nucleoside. The work presented here will shine a new light on the synthesis of sugar-modified ribonucleic acids derived from naturally occurring modified nucleosides.

CHED 269

Chemiresistive gas sensors on shrinkable polymer films

Polina Pivak1,2, Merry Smith2, Kennedy Jensen2, Daphnie Martin2, Katherine Mirica2, [email protected]. (1) Lebanon High School, Lebanon, New Hampshire, United States (2) Chemistry, Dartmouth College, Hanover, New Hampshire, United States

This poster describes an exceedingly simple and rapid approach for fabricating miniaturized chemiresistive gas sensors on shrinkable polymeric films. We demonstrate a method for fabricating miniaturized interdigitated electrodes on plastic substrates by drawing graphite wires with a commercial HB pencil directly on shrinkable polymeric films. By drawing fine lines using commercial pencil leads ranging from 0.3 – 3 mm in diameter, the shrunken products display features (wires ~0.1 mm in width) that would be difficult to draw directly. Deposition of nanomaterials directly into this device architecture produces functional chemiresistive gas sensors from modular molecular building blocks. The devices can detect and differentiate gaseous analytes at part-per-million concentrations.

CHED 270

Mechanism of fingerprint development using gold polyaniline nanocomposites: Physical adsorption versus chemical reaction

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Joshua Borski1, [email protected], Mary Johnson1, [email protected], Victoria Angus1, [email protected], Joshua Tiamco1, [email protected], Jazem Saripada 1, Jerrod Ford1, Yasmin Pajouhafsar1, Asma Alnuaimi2, Najwa Abou Alloul2, Fatma Nahas2, Hanan Abdou2, Ahmed Mohamed2. (1) Chemistry, Blinn College - Bryan campus, College Station, Texas, United States (2) Chemistry, University of Sharjah, Sharjah, United Arab Emirates

The presence of amino acids in the eccrine fingerprint secretions triggered the initial research interest in fingerprint development. In contrary with the general belief that fingerprints development is aided by the electrostatic interaction of the nanoparticles with the various components of the fingerprints, it was proven that it is mainly driven by chemical reactions. Fingerprints were developed using gold-poyaniline nanocomposites of various substituted anilines such as CH3, NO2, COOH, OH, and more. The nanocomposite showed high chemical stability to oxidation, better adhesion to surface, and good contrast ridge details. It is possible that the successful staining is due to a combination of hydrophobic and electrostatic interactions with the eccrine.

CHED 271

Organic field-effect transistor fabrication using hexatriacontane as a dielectric layer

Sandi Grace1, [email protected], Marcos Castillo2, Bumjung Kim1. (1) Chemistry, New Jersey City University, Jersey City, New Jersey, United States (2) Union City High School, Union City, New Jersey, United States

The most important problem with organic transistors that needs to be overcome is the efficiency and effectiveness of these devices. In this study, we tried to eliminate the inefficiency of devices which occurs at the inorganic and organic contact points, Schottky barrier effect, by replacing inorganic silicon dioxide (SiO2) dielectric layer with an organic dielectric layer, hexatriacontane (C36H74). Hexatriacontane layer created an organic-organic interface between the dielectric and semiconductor layers, that could eliminate interlayer Schottky resistance. We fabricated organic field-effect transistor using hexatriacontane dielectric layer and single-crystal rubrene (C42H28) as a semiconductor material. Electrical properties of devices were measured and the effect of hexatriacontane layer was investigated. Significant improvement in hole mobility, on/off ratio, and working voltage was achieved when the device was thermally annealed at 50 °C. After the annealing process, the mobility was increased by 2.5 times and the on/off voltage ratio was increased by 100 times. As for the working voltage, it showed a decrease of approximately 1.5 times compared to the results of the original fabricated device. Mainly attributed by solid-solid transition of hexatriacontane layer, hexatriacontane epitaxy was formed on crystalline rubrene surface and interfacial defects were eliminated. To support our assumption, we used selected area electron diffraction (SAED) and investigated interfacial epitaxy growth of hexatriacontane on crystalline rubrene.

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CHED 272

Complementing electrochemical studies of self-organized gold nanoparticle~cytochrome c superstructures with UV-visible spectroscopy

Nina Kosciuszek, [email protected], Elizabeth R. Pacer, Bayan H. Abunar, Julia Spiridigliozzi, Amanda S. Harper-Leatherman. Chemistry & Biochemistry, Fairfield University, Fairfield, Connecticut, United States

The addition of the protein, cytochrome c (cyt. c), to gold nanoparticles in solution results in self-organization of cyt. c into multilayered protein superstructures (abbreviated as Au~cyt. c superstructures) and stabilizes the thousands of organized cyt. c proteins to unfolding both when encapsulated in porous solids and when remaining in solution. Our research has shown that the electrochemical characteristics of superstructure-assembled cyt. c are enhanced compared to cyt. c alone and vary as the ratio of cyt. c to Au varies and as the size of the Au nanoparticle varies. In order to determine whether the enhanced electrochemical properties are directly related to multiple protein layers of certain types of superstructures staying intact at the electrode surface, protein superstructures made from 5-nm gold nanoparticles were stripped from electrode surfaces, measured with UV-visible spectroscopy, and compared to superstructures made from 10-nm gold nanoparticles. The UV-visible absorbance of the cyt. c Soret peak, and subsequent calculated cyt. c electrode surface coverages will be presented to help narrow in further on the cause of the enhanced electrochemical properties of certain types of superstructure-assembled cyt. c proteins. These results may prove useful to those developing bioanalytical devices when a good understanding of the interaction between protein and material surface is needed.

CHED 273

Partial sulfonation of polyaniline nanofibers

Derek Perry, [email protected], David M. Sarno. Chemistry, Physics and Astronomy, Queensborough Community College of CUNY, Bayside, New York, United States

Polyaniline (PANI) is a well-known conductive polymer that is easily prepared as high surface area nanofibers. Composites of PANI nanofibers with gold nanoparticles (Au-NPs) may result in new materials with novel optical and electronic properties for sensors and other devices. We have observed that sulfonated PANI, with its negatively charged substituents, can attract positively charged Au-NPs, thereby increasing the extent of NP deposition. However, sulfonation increases the water solubility of PANI, ultimately degrading the desirable nanostructure. We hypothesize that degradation may be limited if PANI is only partially sulfonated, leaving the fiber core insoluble while providing sufficient charge at the surface to attract positive NPs. PANI nanofibers are prepared from 0.8 M aniline and 0.1 M ammonium persulfate in acidic solution. The product is deprotonated in ammonium hydroxide, and then sulfonated by exposure to dilute

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sodium metabisulfite. The addition of sulfonate groups has been confirmed by FTIR spectra. Longer exposures to the salt increase the extent of sulfonation, which leads to increasingly soluble and degraded nanofibers as seen in SEM images. The deprotonated form of PANI is known to be more readily sulfonated than its protonated form. We are therefore exploring partial deprotonation via timed exposure to NH4OH as another route to limit and eventually control the extent of sulfonation.

CHED 274

Motion of amino acids through single-walled carbon nanotubes

Jonathon Stoeber, [email protected], Cody Hergenrother, [email protected], Mark D. Ellison. Chemistry, Ursinus College, Collegeville, Pennsylvania, United States

The motion of several amino acids through single-walled carbon nanotubes (SWNT) has been investigated using voltage clamp techniques. Specifically, the amino acids glycine, β-alanine, glutamic acid, and valine have been studied. For all amino acids, the pore-blocking current is found to increase with increasing applied voltage. Additionally, the dwell time of the amino acids was found to be independent of applied voltage, in contrast to previous and current studies on alkali metal ions. The data suggest that the amino acids become uncharged in the SWNT, and results of a mathematical model are compared to the data.

CHED 275

Schmidt reaction for carboxylic acids on single-walled carbon nanotubes

Elliott Purdie, [email protected], Mark D. Ellison. Chemistry, Ursinus College, Collegeville, Pennsylvania, United States

Single-walled carbon nanotubes (SWNTs) can easily be functionalized with carboxylic acids through the use of strong acids. Converting those carboxylic acid groups to other functional groups can increase the usefulness of SWNTs. We have explored the use of the Schmidt reaction to convert carboxylic acid groups on SWNTs to amine groups. Fourier transform infrared (FTIR) spectroscopy was used to examine the SWNTs after the reaction. Success of this reaction is strongly dependent upon the SWNT starting material. The success of this reaction is the starting point for exploring applications of amine-functionalized SWNTs, such as their use in SWNT nanopore devices.

CHED 276

Electroosmotic flow of methanol through single-walled carbon nanotubes

Sam Menges, [email protected], Laura M. Nebel, [email protected], Mark D. Ellison. Chemistry, Ursinus College, Collegeville, Pennsylvania, United States

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The motion of methanol through single-walled carbon nanotubes (SWNT) has been observed using voltage clamp techniques. Methanol molecules were observed to block proton current through the SWNT. This pore-blocking current was found to be dependent on the applied voltage. The time that the methanol molecules spend traveling through the SWNT was found to be independent of applied voltage, as would be expected for a neutral molecule in an electric field. However, a minimum voltage, the threshold voltage, was found, below which no pore blocking was observed. The observation of a threshold voltage is in agreement with theoretical predictions, which indicated that the entry of methanol molecules into the SWNT would be strongly influenced by hydrogen bonding at the pore mouth. Our observations of methanol transport through SWNTs demonstrate the potential for SWNTs to facilitate the nanoscale motion of neutral molecules.

CHED 277

Effect of the presence of single-walled carbon nanotubes on the action of an antifungal agent on Saccharomyces cerevisiae

Chase Renninger, [email protected], Mark D. Ellison. Chemistry, Ursinus College, Collegeville, Pennsylvania, United States

Carbon nanotubes have a wide range of potential uses given their large surface area on which to perform chemistry and the variety of possible functionalization reactions. The role of carbon nanotubes with the delivery of various drugs targeted towards different microorganisms has generally been shown to cause increased drug efficacy. We tested this trend by exposing Saccharomyces cerevisiae to a novel azole anti-fungal compound in the presence of oxidized single-walled carbon nanotubes (o-SWNTs) and found that there is a reduction in the anti-fungal capacity of 3,5-dimethylpyrazole-2-methanol. We hypothesize that, due to the large amount of surface area of the o-SWNTs, they are able to interact with the aromatic azole compound via π-stacking and thereby reduce the compound's ability to inhibit yeast growth.

CHED 278

Antibiotic delivery to Escherichia coli using PEG-modified nano-graphene oxide

Katherine Fiocca, [email protected], Nerica Normil, [email protected], Mark D. Ellison. Chemistry, Ursinus College, Collegeville, Pennsylvania, United States

Due to the increasing problem in human health of antibiotic resistance in bacteria, novel modifications of the delivery of antibiotics have become an increasingly popular field of study. Nano-graphene is a useful compound in that it is water soluble, and can be modified to work in many different applications, both biologically and mechanically. Our previous experiments confirmed the modification of graphene into nanoscale graphene oxide (NGO) with the successful attachment of polyethylene glycol (PEG) to increase water solubility. This compound was used to deliver the soluble antibiotic, tetracycline

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hydrochloride, into resistant bacteria. Escherichia coli, a gram-negative bacterium, was used and contained a plasmid coding for antibiotic resistance via an efflux pump. Our results were able to confirm the presence of PEG and tetracycline hydrochloride on the nano-graphene. The amount of tetracycline hydrochloride attached to the NGO-PEG was quantified using UV spectroscopy, and a minimum inhibitory concentration of NGO-PEG TET HCl was calculated for DH5α, the non-resistant E. coli, and DH5α containing pBR322, the resistance plasmid. The goal of this experiment was to increase the antibiotic attachment onto the nano-graphene oxide, in addition to increasing the inhibition of the resistant bacteria at lower concentrations of nano-graphene oxide with attached antibiotic. This was accomplished by using the molecular (not the hydrochloride salt) form of tetracycline, and repeating previous experiments to find the minimum inhibitory concentration of NGO-PEG TET in the presence of the DH5α and DH5α/pBR322. Growth experiments were conducted with bacteria both lacking and containing the resistance plasmid, and the amount of growth was measured using spectrophotometry and viable bacterial counts.

CHED 279

Functionalization of single-walled carbon nanotubes for use in overcoming antibiotic resistance in Escherichia coli

Madison Force, [email protected], Ria Rathi, [email protected], Mark D. Ellison. Chemistry, Ursinus College, Collegeville, Pennsylvania, United States

Carbon nanotubes have been emerging as promising material to be used in drug delivery. Single-walled carbon nanotubes (SWNTs) have a high cell membrane permeability and can easily be functionalized to carry chemical compounds. We have studied SWNTs functionalized with the antibiotic tetracycline for their effectiveness against antibiotic-resistant in Escherichia coli. The E. coli strain DH5α was studied, both with an without the resistance plasmid PBR322, which includes a gene that encodes for an efflux pump. Previous studies in our research group have found that tetracycline-functionalized SWNTs are effective against non-resistant DH5α strains and effective against DH5α/PBR322 strains at high concentrations. Adaptations in our protocol have been made in order to increase the effectiveness of tetracycline delivery at lower concentrations. These adaptations include acid-cutting the SWNTs, functionalizing the SWNTs with polyethylene glycol to increase the water solubility of the SWNTs, and maximizing the loading of tetracycline onto the SWNTs. The results of our adaptations show promise and will be discussed.

CHED 280

Studies toward the synthesis of novel cross-membrane fluorometric probes

Ana Cartaya, [email protected], Nicole Hill, Tumininu Faniyan, Tyler Zimmermann, Danielle Raymond, Tim Liwosz, Tina G. Goudreau Collison, Anju Gupta. Chemistry, Rochester Institute of Technology, Rochester, New York, United States

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The mechanism by which therapeutic molecules cross the cell membrane is of great importance in designing drugs and drug delivery systems. Fluorescent cross-membrane probes are molecules containing both hydrophilic and hydrophobic components that can straddle a phase partition and can be used to investigate such mechanisms. Our research focuses on the synthesis of novel cross-membrane probes bearing fluorescent activity. The probes will span a phospholipid/cholesterol-based model membrane and be used to monitor subtle physiochemical changes on either side by ratioing the signals. Data collected on the interaction between the amphiphilic fluorophores and model cells can further be analyzed and serve to target methods for improved drug delivery systems.

CHED 281

Noncovalent CH-aromatic interaction as a function of solvation

Sara Bey, [email protected], Sarah Ashour, [email protected], Bright U. Emenike. Chemistry & Physics, State University of New York at Old Westbury, Old Westbury, New York, United States

Molecules “communicate” through a set of weak interactions known as non-covalent interactions, i.e., the interactions without the formation of a chemical bond. An example of a non-covalent interaction is the CH-aromatic interaction; the interaction between a CH group and the face of an aromatic ring. Although CH-aromatic interactions are well recognized, the experimental measurement of a single CH-aromatic interaction is still a challenge because of the weak interaction energy involved (ΔG ≈ 1 kcal/mol). Consequently, there are limited investigations into the physical origins of the CH-aromatic interactions. In this study, we present the conformational studies of a molecular torsion balance in different organic solvents. The molecular balance adopted folded and unfolded conformers in which the ratio of the conformers provided a quantitative measure of CH-aromatic interaction as a function of solvation. While a single empirical solvent parameter based on solvent polarity failed to explain the observed solvent effect, it was shown that CH-aromatic interactions can be correlated through a multiparameter linear solvation energy relationship (LSER) using Kamlet-Taft equation. The resulting LSER equation expresses CH-aromatic interactions as a function of Kamlet–Taft solvent parameters, which revealed that specific solvent effects, α and β (where α represents a solvents' hydrogen-bond acidity and β represents a solvents' hydrogen-bond basicity) are mainly responsible for “tipping” the molecular balance in favor of one conformer over the other.

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CHED 282

Studies toward the total synthesis of trocheliophorolide A: Making the unsaturated side chain moiety as a convergent Suzuki coupling partner

Julianne Caponigro, [email protected], Hannah M. Simpson, William Spencer, Tina G. Goudreau Collison. Chemistry, Rochester Institute of Technology, Rochester, New York, United States

Trocheliophorolide A is a natural product isolated from soft coral. It is an interesting synthetic target because it has biological activity against Staphylococcus aureus and Baciliius subtillis. We envision the synthesis of trocheliophorolide A as a convergent synthesis. Progress toward the challenging unsaturated side chain moiety will be highlighted. The synthetic route toward the vinyl borate will also be discussed as it pertains to the convergent Suzuki coupling toward the final product.

CHED 283

Model study toward the total synthesis of aplydactone: Advances toward the dilithiate side chain

Michael Cattalani, [email protected], Andrew Streit, [email protected], Austin Kelly, Katherine A. Valentine, Tina G. Goudreau Collison. Chemistry, Rochester Institute of Technology, Rochester, New York, United States

Aplydactone is a sesquiterpene natural product isolated from the sea hare Aplysia dactylomela that is found on the northern coast of Madagascar. Interest in synthesizing aplydactone is driven by its extremely novel and conformationally strained tetracyclic

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framework. Aplydactone’s ring system has bond angles more acute than ever before seen for cyclobutane. Additionally, the carbon-carbon bonds in aplydactone’s cyclobutane rings are reported to be longer than average carbon-carbon bonds. This presentation describes the synthesis of the convergent route toward the model tetracycle and focuses mainly on the progress made toward the synthesis of the dilithiate coupling moiety.

CHED 284

Using BAPN derivatives to synthesize small molecule LOX inhibitors

Meagan L. Williams, [email protected], Danielle M. Solano. Chemistry & Biochemistry, California State University, Bakersfield, Bakersfield, California, United States

It is widely known that the LOX enzyme contributes to the metastasis of cancer cells from hypoxic tumors in patients. Studies have shown that β-aminopropionitrile (BAPN) is active in preventing this spread, however BAPN alone is harmful to the patient. Therefore, carrier molecules are necessary to transport the BAPN safely to the site of the hypoxic tumor ready to metastasize. Previous research has focused on changing reactant 1 (Figure 1); however, these products exhibit about the same level of inhibitory effect. Due to this, we have decided to try using BAPN derivatives to see if the change in that reactant has a greater effect on the LOX enzyme. This research will highlight the use of BAPN derivatives of varying differences (Figure 2) and the products will be tested for effectiveness of LOX inhibition.

CHED 285

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Synthesis of asymmetrically substituted cycloheptatrienylidene fluorophores

Navindra David, [email protected], Ivan D. Hyatt. Chemistry, Adelphi University, Garden City, New York, United States

Currently, methodologies that synthesize symmetrical cycloheptatrienylidenes use palladium catalysts which can be expensive and time consuming. The project herein seeks to find a cheaper, faster way to synthesize these structures with an additional goal of making them asymmetric. The methodology utilizes the reactivity of hypervalent iodonium alkynyl triflates when treated with various nucleophiles while in a solution of benzene. The subsequent vinylidene carbene that forms reacts with the benzene to initially form a [4.1.0] bicycle. Previous studies have shown that an equilibrium can exist between the [4.1.0] bicycle and the ring-opened cycloheptatrienylidene, and that substituents can affected the favored product. Once synthesized, the cycloheptatrienylidene fluorophore can be reacted with various metals, such as copper or lanthanides in order to monitor the effects of fluorescence through an aggregation induced emission process. It is predicted that aromatization of the cycloheptatrienylidene will cause aggregation and turn on the light-emitting fluorescence as the molecule undergoes a restriction of intramolecular rotation. Variations of substituted hypervalent iodonium alkynyl triflates and different nucleophiles can lead to a methodology that quickly assembles asymmetrically substituted cycloheptatrienylidene fluorophores in a limited number of steps.

CHED 286

Modifying the structure of ciprofloxacin to synthesize novel bacterial resistant antibiotics

Vanessa K. Cupil-Garcia, [email protected], Alexandra B. Ormond. Chemistry, Physics and Geoscience, Meredith College, Holly Springs, North Carolina, United States

During the 2016 World Economics Forum, a Chemical and Engineering News article reported the Pharma industry’s declaration of war on antibiotic resistant bacteria.

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Bacteria that are resistant to antibiotics complicate the treatment and recovery of people who have bacterial infections, leading to further health issues or death. Ciprofloxacin is an antibiotic used to treat infections, such as anthrax, pneumonia, and cystic fibrosis. Bacteria have become increasingly resistant to antibiotics, including ciprofloxacin and other quinolone derivatives. Thus, resistance can be countered by modifying the chemical structure of existing antibiotics, yielding molecules that are potentially as effective as the parent drug without the existing challenge of bacterial resistance. A ciprofloxacin derivative will be synthesized via a two to three step synthetic pathway. The intermediates and final products will be purified and structurally characterized using nuclear magnetic resonance (NMR) analysis and Fourier transform infrared (FTIR) spectroscopy. The antibacterial activity of the ciprofloxacin derivative will be compared to the antibacterial activity of ciprofloxacin using a minimum inhibitory concentration (MIC) assay. Modifications to the structure of ciprofloxacin will help determine the efficacy of the derivative and the substitutions that contribute to the antimicrobial performance of the quinolone derivative.

CHED 287

Microwave-assisted Friedel-Crafts synthesis of methylacetophenone by using eco-friendly clay catalyst

Charlotte Sandland, [email protected], Matthew Douglass, Mustafa Yatin. Chemistry and Physics, Salem State University, Salem, Massachusetts, United States

Studies on the Friedel-Crafts acylation reactions using traditional Lewis acid catalysts, like AlCl3, and conventional heating are widely available in scientific literature and thoroughly discussed in the electrophilic aromatic substitution parts of two semester organic chemistry text books and practiced in undergraduate organic laboratory experiments. This study focused on optimization of inquiry-based microwave-assisted green synthesis of methylacetophenone by Friedel-Crafts acylation of toluene using activated Montmorillonite K10 Clay (MMT K10), a naturally occurring zeolite consisting of layered aluminosilicate smectite, Al2Si4O10(OH)2●nH2O, as a substitute catalyst to generate acylium ions from acetic anhydride. The MMT K10 is solid and can easily be separated from the reaction mixture and reused allowing to reduce the environmental and economic impact, as well as increase the safety of the undergraduate laboratory. The MMT K10 was heat activated and the Friedel-Crafts synthesis was carried out by using microwaves (Single Mode MW System–CEM Discover). The microwaved contents were centrifuged to separate the solid clay catalyst, the mixture was fractioned by liquid-liquid extraction, and both organic and aqueous layers were dried by using rotary evaporator. In this ongoing project, the isolated products are identified using thin layer chromatography, Varian Mercury 300 MHz 1H-NMR and Thermo Scientific IR100 FT-IR, and the results are compared against traditional AlCl3-catalyzed method. The green chemistry metrics, such as atom economy, effective mass yield, and e-factor, are used to evaluate and compare the green aspect of the traditional and the method investigated in this study.

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CHED 288

Isomerization of vicinal dibromides in conformationally rigid cyclohexane systems

Ryan P. Acocella, [email protected], Anne R. Szklarski. Chemistry and Physics, King's College, Wilkes-Barre, Pennsylvania, United States

It is known that vicinal bromine atoms in rigid cyclohexane systems can undergo a diatropic shift when heated. This 1,2 interchange results in the rearrangement of the bromine atoms from the diaxial positions to the diequatorial positions. The goal of this project was to determine if this diaxial-diequatorial isomerization could be developed into an undergraduate laboratory experiment that would demonstrate the concept of kinetic and thermodynamic products. The substrate, 1,2-dibromo-4-(tert-butyl)cyclohexane, was synthesized by the bromination of 4-(tert-butyl)cyclohexene at 0 °C to give a 9:1 mixture of diastereomers, favoring the kinetic product. The kinetic product contains diaxial bromine atoms, whereas the minor, thermodynamic product has both bromines in the equatorial position. The isomerization was completed under polar and nonpolar conditions by heating the substrate neat or in d6-DMSO at various temperatures. The ratio of diequatorial to diaxial isomers was monitored using gas chromatography/mass spectrometry (GC/MS). The results of the isomerization reactions and the current status of the undergraduate laboratory experiment will be discussed.

CHED 289

Effect of aryl and N-heterocyclic systems on the solvatochromatic properties of 3H-imidazo[4,5-b]pyridines

Mercedes N. Bauman1, [email protected], Patrick A. Ross1, Susan Ragheb2, Michael J. Castaldi1, James K. Murray1. (1) Chemistry, Immaculata University, Immaculata, Pennsylvania, United States (2) Chemistry, St. Peter's University, Jersey City, New Jersey, United States

With solvatic chromatic characteristics of various imidazo [4,5-b] pyridines observed in previous work further derivatization was completed. In our original series a handle for further derivatization was left through the presence of an aryl bromide. This was used to extend conjugation through the use of the Suzuki coupling reaction. Additionally, a series of compounds were prepared through a multistep synthesis including nucleophilic aromatic substitution with N-heterocyclic systems, reduction of nitro, and ending with the preparation of imidazo [4,5-b] pyridines. Solvatic chromatic characteristics were then measured with the use of UV-Vis spectroscopy.

CHED 290

Hydroporphyrin dyads as singlet oxygen photosensitizers and fluorophores with solvent polarity-dependent photochemical properties

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Linda Wiratan, [email protected], Nopondo N. Esemoto, Zhanqian Yu, Marcin Ptaszek. Chemistry & Biochemistry, University of Maryland Baltimore County, Baltimore, Maryland, United States

Hydroporphyrins (chlorins and bacteriochlorins) exhibit singlet oxygen photosensitizing and near-IR fluorescence properties that are of interest for biomedical applications, including photodynamic therapy (PDT). Photosensitizers that activate only upon localization at target treatment sites have long been sought as highly selective PDT agents; we hypothesize that the polarity of the sub-cellular environment could be one such activating factor. Here, we report the investigation of a series of metalated (Pd and Zn) chlorin dyads, their corresponding free base dyads, and non-metalated bacteriochlorin dyads with differing linkers to determine the effect of solvent polarity on

the singlet oxygen (Φ△) and fluorescence (Φf) quantum yields. Both yields were found to be dependent on solvent polarity; higher solvent polarity generally results in lower yields

of Φ△ and Φf. Of the solvents tested, Φ△ was greatest in toluene (ε = 2.38) while negligible in DMF (ε = 36.7). Measuring Φf in these solvents also resulted in the same

observation, although this relationship appears much weaker for the chlorin dyads. Φ△ and Φf were also found to vary greatly depending on the type of linker connecting the two dyad monomers and whether the dyad is metalated. Tests against corresponding monomers of the dyads showed that the monomers did not exhibit solvent polarity dependence. These findings may contribute to the development of activatable probes with greater sensitivity to cellular environments.

CHED 291

Synthesis of stercobilin: A potential biomarker for autism

Jordan Coffey1, [email protected], Andrew Vadas2, Katelyn Lewis3, Gregory Pirrone4, Troy Wood5, Amber Charlebois1. (1) Chemistry, State University of New York at Geneseo, Geneseo, New York, United States (2) Biology, State University of New York at Geneseo, Geneseo, New York, United States (3) Chemistry, Fairleigh Dickinson University, Old Bridge, New Jersey, United States (4) Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts, United States (5) Chemistry, State University of New York at Buffalo, Buffalo, New York, United States

Autism is a condition that is, at present, only diagnosed by psychological tests and observations or by parental assessment. At this time, there is no quantitative method to diagnose autism. Dr. Troy Wood and his team at SUNY Buffalo have observed that children with autism have a lower concentration of stercobilin (a bile pigment synthesized in the small and large intestines) in their urine. We are collaborating with the Wood team to create an internal standard that can be used to measure the amount of stercobilin in a patient’s urine. Currently, we are developing and optimizing a method for synthesizing stercobilin. During the synthesis, we are incorporating different levels of deuterium (heavy hydrogen) so that the stercobilin can be labeled which would allow the amount naturally occurring in a patient’s urine to be quantified. Once complete, we will be on our way to create the first quantitative method for diagnosing autism.

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CHED 292

Microbial chemical ecology: Molecular interactions between Batrachochytrium dendrobatidis and Janthinobacter lividum

Brenda Ho2, [email protected], Thomas P. Umile1. (1) Division of Natural & Computational Sciences, Gwynedd Mercy University, Gwynedd Valley, Pennsylvania, United States (2) Chemistry, Chestnut Hill College, Philadelphia, Pennsylvania, United States

Batrachochytrium dendrobatidis (Bd) is an aquatic fungal pathogen that causes the lethal amphibian skin infection chytridiomycosis, which is a leading cause of global amphibian population decline. One defense against Bd are symbiotic bacteria that live on the skin, such as Janthinobacter lividum which produces the antifungal metabolite violacein. Bd produces its own metabolites, methylthioadenosine (MTA) and kynurenine, which may play a role in Bd’s pathogenicity. These metabolites may also be important in Bd’s competition with bacterial antagonists. To test this, J. lividum was grown in the presence of MTA, kynurenine, and an unfractioned Bd supernatant. The effect of Bd metabolites on J. lividum was then measured through cell-counting assays and by monitoring violacein production by HPLC.

CHED 293

Cationic methyl-aryl interactions as a function of solvation

Jacob T. Jones, [email protected], Ronald Spinelle, [email protected], Bright U. Emenike. Chemistry & Physics, State University of New York at Old Westbury, Old Westbury, New York, United States

The ubiquitous nature of cation-aromatic interactions - the stabilizing interactions between cations and the π face of aromatic rings - has led to a variety of applications in science. Although many studies have established the strength of cation-aromatic complexes, the effects of solvation have not been properly investigated, which is surprising considering that the strength of cation-aromatic interactions is known to be modulated by solvation. In this study, the interaction between an N-methyl pyridinium (cation) group and the π face of a benzene ring were experimentally measured in different organic solvents. The experimental cation-aromatic interaction energies were obtained through the conformational studies of synthetic molecular torsional balances, which are capable of measuring weak cation-aromatic interactions in solutions. Subsequently, a relationship between the strength of the cation-aromatic interactions and the physical parameters of the solvating media was established. This study provided important insights into the physical origin and mechanism of the cation-aromatic interactions.

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CHED 294

Purification and analysis of distinct porphyrin molecules

Shadi N. Khayyo, [email protected], Arian Novaj, Steven Maio, Dorina Ismailgeci, Valerie Khayyo, Pamela K. Kerrigan, Daniel Amarante. Division of Natural Sciences, College of Mount Saint Vincent, Riverdale, New York, United States

The goal of this research is to purify the meso-substituted isomers of p-anisaldehyde, p-tolualdehyde and p-pyridinecarboxaldehyde porphyrins that are synthesized by a modified Adler method. These compounds are separated using column chromatography. Different silica gel and chloroform/methanol mixtures were used based on the type of porphyrin being purified. For the tolyl and methoxy porphyrins, a 60 Å mesh silica size was used. The tetra-tolyl porphyrin separated with 100% chloroform, while the tri tolyl porphyrin used a 5% methanol/chloroform mixture. The tetra-methoxy was obtained with 100% chloroform and the tri methoxy porphyrin required a 2% methanol/chloroform mixture. The silica used for pyridine porphyrin was a 150 Å mesh. The tetra pyridine was obtained with 100% chloroform and the mono-pyridine porphyrin required a 2% methanol/chloroform mixture. Purity was tested by TLC, UV-Vis, and NMR. For the tolyl porphyrin, the average percent yield was calculated to be 5%. The methoxy porphyrin average percent yield was 4.77%. The pyridine porphyrin average yield was 5.4%. These molecules will be incorporated into liposome carriers for use in the destruction of cancer cells.

CHED 295

Trimethylenemethane reactions from hypervalent iodonium alkynyl triflate: Generation of substituted diquinanes

Tian Li, [email protected], Ivan D. Hyatt. Chemistry, Adelphi University, Garden City, New York, United States

In this project, hypervalent iodonium alkynyl triflate is reacted with a nucleophile to temporarily form a vinylidene carbene intermediate. Once formed, the vinylidene

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carbene reacts intramolecularly with an alkene to generate a trimethylenemethane diyl. The resulting reactive intermediate leads to diradical quenching to form the final product, substituted diquinanes. Various substituted hypervalent iodonium alkynyl triflates can lead to different ring structures depending on the unsaturation and the nucleophiles used. The project will investigate functional group tolerance and explore other potential ring systems made by this methodology.

CHED 296

Formation of conglomerates for optical resolution

Anna Lim, [email protected], Aleksandr Gorbenko, Homar S. Barcena. Physical Sciences, Kingsborough Community College, Brooklyn, New York, United States

Chirality, or handedness, is an important chemical concept with applications in medicine, materials science, and natural products. The resolution of stereoisomers was performed first by Louis Pasteur when he manually separated the enantiomers of tartaric acid from a conglomerate mixture of crystals. It has been previously reported that 2,3-bis-fluoren-9-ylidenesuccinic acid may be resolved by conglomerate formation, and in our study, we performed the synthesis of diethyl 2,3-bis(fluorenylidene)succinate to investigate its ability to form homochiral inclusion crystals.

CHED 297

Synthesis of fulgides for optoelectronics

Homar S. Barcena, Justin Powell, [email protected]. Physical Sciences, Kingsborough Community College, Brooklyn, New York, United States

Fulgides have been explored as molecular switches. These highly conjugated compounds have interesting photochromic properties that may be useful for molecular memory devices. We report on the synthesis and purification of 2,3-

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bis(diphenylmethylene)succinic acid via Stobbe condensation, with spectroscopic data (NMR, IR, MS) to confirm the product.

CHED 298

Electron-rich asymmetric viologens via reductive eliminations of diaryl-l3-iodanes

Andrew S. Koch, Leah M. Dignan, [email protected]. Chemistry & Biochemistry, St. Mary's College of Maryland, St. Mary's City, Maryland, United States

Due to their multiple redox states, viologens have varied applications in such fields as electron mediators and electrochromic materials. We describe a novel simple route to new viologens that have previously been unavailable. Here, we present a novel synthetic method for electron-rich N-aryl asymmetric viologens through the use of hypervalent diaryl-l3-iodanes. The electrochemistry of the new viologens will also be discussed.

CHED 299

Investigating the relationship between the antimicrobial and estrogen receptor binding properties for 3,5-substituted parabens

Bridget Bergquist, [email protected], Kaelyn Jefferson, Andrew A. Yeagley. Chemistry and Physics, Longwood University, Farmville, Virginia, United States

Parabens are used in cosmetics to prevent bacterial growth. They have also been shown to bind the Estrogen Receptor (ER); a fact that possibly links them to breast cancer. Dihalogenated parabens have been found to have a reduced affinity for the ER but maintain their antibiotic properties. This work investigates the effect of various substitutions that influence both ER binding and antibiotic activity. These substitutions have led to a disconnection in the activities observed.

CHED 300

Studies toward an affordable preparation of D-vinylglycine

Rebecca Ford, [email protected], Samer Isa, Ethan Decicco, Luis Sanchez. Biochemistry, Chemistry & Physics, Niagara University, Niagara University, New York, United States

While life on Earth is exclusively based on L-amino acids and D-sugars, it has recently been found that D-amino acid-containing molecules do exhibit a variety of important bioactivities. Natural antibiotics involving D-amino acids units have been isolated from bacteria and many reports have revealed the participation of D-amino acids in certain biological processes and cell functions. D-amino acids possess “unnatural” chiral

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centers that make them attractive as building blocks for the synthesis of bioactive compounds. Incorporation of D-amino acids into peptide chains and cyclic peptides can severely affect their interactions with biological targets and their slower degradation compared to the corresponding L isomers can be of great use in therapeutics. D-amino acids are most commonly obtained via racemization of natural L-amino acids followed by chiral separation; however, production of commercially viable amounts is still complicated and expensive. In the specific case of vinylglycine, racemization is not a viable option due to isomerization. This project aims at developing a unique, inexpensive approach to synthesizing D-vinylglycine from L-serine as starting material. Given the exploitable reactivity of vinylglycine, ready synthetic access to the D enantiomer will provide the material needed to study its incorporation into peptides for late-stage site-specific structural modification and the synthesis of complex D-branched amino acid-like moieties.

CHED 301

Synthesis of dihydropyrans and tetrahydropyrans using Lewis acid promoted tandem reactions

Rachel J. Edwards, [email protected], Ryan M. Crane, John F. Halonski, Tyler Nungesser, Jeffrey M. Carney. Molecular Biology and Chemistry, Christopher Newport University, Newport News, Virginia, United States

Synthesis of biologically-active compounds for medicinal uses in antibiotics, anti-fungals, and anti-cancer drugs is a primary goal of organic chemistry. Dihydropyran and tetrahydropyran rings are common structural features in a variety of compounds that exhibit antibiotic and anticancer properties. The construction of heterocyclic systems has been a continued interest of synthetic chemists in order to enable the faster and cheaper production of pharmaceutical compounds. We have explored a one-step reaction process to synthesize dihydropyran rings to improve upon current methods. A reagent designed to undergo sequential nucleophilic attack in a ring-forming cascade of reactions was used, and optimal conditions for the cyclization were explored. Optimization involved the use of a variety of Lewis Acids, as some led to the isolation of undesired tetrahydropyran products. Various carbonyl electrophiles and nucleophilic reagents were also employed. As a rapid method to introduce common heterocycles, this process has a promising potential for use in the synthesis of many biologically-active compounds.

CHED 302

Cyclization of tethered aminoalkenes with in situ generated catalytic hypervalent iodine

Darcy Davidson, [email protected], Dmitry V. Liskin, Megan Sak, Skye Harris, Jeffrey M. Carney. Molecular Biology and Chemistry, Christopher Newport University, Newport News, Virginia, United States

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Oxyamination of an alkene can be used to synthesize 3-hydroxypiperidines and 3-hydroxypyrrolidines when tethered aminoalkenes are used as substrates. Many existing methods rely on metal catalysts to promote the oxyamination of alkenes. However, recent studies have shown that metal free oxyamination of alkenes is possible using a Brønsted acid and hypervalent iodine. When using these reaction conditions, only exo-cyclization products are observed. Our group is currently investigating the use of catalytic iodobenzene and meta-chloroperoxybenzoic acid (mCPBA) as the main oxidant that will produce hypervalent iodine in situ and trifluoroacetic acid as a strong Brønsted acid promoter. mCPBA is normally used to epoxidize alkenes; however, in this system oxidation of iodobenzene into a hypervalent species is much faster and an endo-cyclization product is observed. We hypothesize the formation of hypervalent iodine species in situ and its subsequent activation by a strong Brønsted or Lewis acid. Other carboxyilic acids, carbon and nitrogen nucleophiles are also under investigation.

CHED 303

Organic synthesis of fluorescent cyanine dyes and their precursors

Jahnn Drigo, [email protected], Angela J. Winstead. Chemistry, Morgan State University, Baltimore, Maryland, United States

Heptamethine (Cy7) cyanine dyes are the interest of scientist because of their significant ability to luminescence in the near-infrared region, 650-900 nm. Pentamethine cyanine (Cy5) dyes are often used as fluorescent probes for pathogen detection. However, Cy5 fluorescence labels suffer from biological interference from molecules that also fluoresce at 650 nm-700 nm. Current synthetic methods utilize excessive amounts of solvent; involve long reaction times (16 -18 h), and contain impurities in the products. This study applies microwave assisted organic synthesis (MAOS) as an eco-friendly, faster, and cleaner approach to synthesizing benzoindolenine heptamethine cyanine dyes. The specific aims of this approach are the synthesis of: 1) benzoindolenine heterocyclic salt derivatives, 2) benzoindolenine heptamethine cyanine dyes and 3) aniline substituted benzoindolenine dyes. 5-bromovaleric acid methyl ester and 6-iodohexanoic acid ethyl ester were synthesized as synthetic reagents to the 5-bromovaleric and the ethyl hexanoate benzo salts, respectively. Several benzoindolenine heterocyclic salt precursors were synthesized with satisfactory yields and reduced reaction times. The benzo-ethyl and -propyl dyes

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were synthesized with 97% and 85% yield, respectively, and in 30 min or less, a reduction from the 18 h stated in the literature. The aniline substituted benzo-ethyl Cy7 dye has been synthesized in 54% yield. Optimization studies of this reaction are ongoing. Future work includes the synthesis of additional benzoindolenine heterocyclic salts and Cy7 dyes that possess the excellent spectral properties. All structures were determined by 1H and 13C 400 MHz NMR. The dyes were also characterized using Cary50 UV/Vis spectrometer.

CHED 304

Synthesis of substituted cinnamyl bromides and aryl β-keto esters toward a convergent total synthesis of naturally-occurring phosphodiesterase-9A inhibitors

Armen G. Beck, [email protected], Maggie McEwan, [email protected], Kierra L. Perry, Andrew Moyer, Kiersten A. Ring, Jeffrey M. Carney. Molecular Biology and Chemistry, Christopher Newport University, Newport News, Virginia, United States

Cyclic adenosine monophosphate (cAMP) and cyclic guanosine monophosphate (cGMP) are intracellular messenger molecules involved in many biological processes. There are 21 phosphodiesterase (PDE) enzymes that deactivate cAMP and cGMP and reducing the effectiveness of PDEs through small molecule inhibition has been an effective approach for treatment of certain diseases. One phosphodiesterase that has seen particular interest is PDE9, which specifically deactivates cGMP. We report our work in a convergent total synthesis of the first selective phosphodiesterase-9A (PDE9A) inhibitors isolated from nature. A laboratory synthesis of these structures will allow for the verification of the structural assignment and an examination their inhibitory affinities and selectivity against PDE9A, permitting a more complete exploration of their subsequent potential for disease treatment. Our retrosynthetic analysis of the core structure of these compounds revealed the possibility of a convergent synthesis through a late stage combination of various cinnamyl bromides, β-ketoesters, and a substituted cinnamaldehyde. The synthesis of these cinnamyl bromides and β-keto esters, and their inclusion into the core structure has been accomplished.

CHED 305

Synthesis of chiral oxetanes via the enantioselective reduction of prochiral 2-halogenated ketones

Jennifer M. Garcia Rodriguez, [email protected], Javier E. López Hernández, Blanca Quiñones Díaz, Kiara M. Santiago, Sandraliz Espinosa-Díaz, Margarita Ortiz-Marciales. Chemistry, University of Puerto Rico - Humacao, Humacao, Puerto Rico, United States

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The enantioselective reduction of prochiral 2-halogenated ketones is a practical and effective way to synthesize nonracemic g-halogenated alcohols, which can be transformed into enantiopure oxetanes. The ring opening of oxetanes with amino compounds can produce a variety of optically active amino alcohols, which are key precursors in the synthesis of biological active compounds, particularly, for the treatment of neurological diseases, such as depression and anxiety. Our work is based on the asymmetric borane–mediated reduction of prochiral β-halogenated aryl ketones to their corresponding optically active alcohols using as catalyst the spiroaminoborate ester derived from ethylene glycol, triisopropyl borate and (S)-(-)-diphenyl-2-pyrrolidinemethanol. The enantiopure alcohols were purified by column chromatography with silica gel and characterized by 1H NMR, 13C NMR, IR, GC/Chiral Column and GC/MS. The cyclization of the nonracemic alcohols to form the oxetane was successfully achieved using 3 equivalents of potassium tert-butoxide as base, obtaining the oxetane in good yield.

CHED 306

Novel synthetic method for the regiospecific preparation of [2H]-indazoles

Edward J. Salaski, Jean Etersque, [email protected], Melissa Orlando. Chemistry and Pharmaceutical Science, Fairleigh Dickinson University, Madison, New Jersey, United States

Since their original description by Nahm and Weinreb, N-methoxy-N-methyl amides have been widely used as intermediates to allow the conversion of carboxylic acid derivatives into ketones and aldehydes via the addition of organometallic reagents. We attempted to use this chemistry with anthranilamide 1 and an excess of ethyl magnesium bromide to produce ethyl ketone 2. The cleanly obtained product was not, however, the targeted ketone. Instead, it was a material whose 1H and 13C NMR and mass spectrum corresponded to the 2-methyl-3-ethyl-[2H]-indazole 4. Our proposed mechanism for this unexpected transformation is shown in the scheme. It involves an

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intramolecular direct displacement of the N-methoxy group of the Weinreb amide to produce the indazolinone intermediate 3. Nucleophilic attack on the carbonyl and elimination of water then provides the observed indazole. This poster describes our efforts to optimize and determine the scope and limitations of the overall conversion of Weinreb anthranilimides to [2H]-indazoles. It also outlines our investigation into the proposed mechanism, by utilizing non-nucleophilic bases to confirm the intermediacy of indazolinones, such as 3. Possibilities for the enhancement of the proposed unusual nitrogen-nitrogen bond formation through direct substitution are also discussed.

CHED 307

Norbornadiene to quadricyclane intercoversion: Effect of substitution at the methylene bridge

Daniel Smee, [email protected], Bret Unger, [email protected], Mary Sexton, Felix Goodson. Chemistry, West Chester University, West Chester, Pennsylvania, United States

We have developed a synthesis of substituted norbornadiene derivatives in which we can vary the substituents at the methylene bridge position. In this poster we present the characterization of these compounds, as well as the results of our investigations on how substituents affect the photochemical properties of the norbornadienes, as well as the stability of the resulting quadricyclanes. These studies address the possibility of using the photochemical conversion of norbornadiene compounds to store solar energy.

CHED 308

Oxaquinonacyclophanes: Synthesis and host-guest binding

Taylor Sanders, [email protected], Jay W. Wackerly. Chemistry, Central College, Pella, Iowa, United States

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A novel class of macrocyclic, supramolecular compounds, we have termed oxaquinonacyclophanes, have been synthesized by our lab in one step from readily available starting materials. One such quinone-based macrocycle exhibits a “tweezer-like” structure in the solid state, which provides a rigid, p-electron poor cavity for potential electron rich guest binding. This macrocycle was titrated with various pyridine-N-oxide guest molecules in benzene and the binding constants were determined via 1H NMR spectroscopy.

CHED 309

Solvent mediation of unimolecular helical exchange dynamics in the synthetic helical peptide Z-Aib6-β-Ala-OMe

Chase Foster-Spence1, [email protected], Jesse D. Dickovick1, Matthew C. Rotondaro1,2, Matthew A. Kubasik1. (1) Chemistry & Biochemistry, Fairfield University, Fairfield, Connecticut, United States (2) Chemistry, Boston University, Boston, Massachusetts, United States

Our work characterizes the effects of solvent viscosity, solvent polarity, and solvent hydrogen-bonding capacity as a function of temperature towards determining the rates of helical conformational exchange of a dissolved solute probe. Our work employs Z-Aib6-β-Ala-OMe, unique for its 310 helical structure and its ability to undergo isoenergetic conformational exchange between left- and right-handed helices. We use 1H and 13C NMR spectroscopy to determine the rates of conformational exchange using NMR line-shape analysis. We vary solvent viscosities by using a series of alcohol solvents and by varying sample temperature. Obtained rate constants are analyzed with Eyring treatments to characterize peptide activation thermodynamics. We interpret the kinetic data with theories that admit an explicit role for solvent viscosity, such as Kramers’ theory. Our unique peptide probe undergoes millisecond activated barrier crossings in its electronic ground state. This work provides novel insight into solvent influence in helical exchange dynamics in a unique synthetic polyamide system.

CHED 310

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FT-IR spectroscopy, computational quantum chemistry, and Hessian reconstruction analyses of helical peptide isotopologues of Aib

Matthew C. Rotondaro1,2, [email protected], Jesse D. Dickovick1, Chase Foster-Spence1, Matthew A. Kubasik1. (1) Chemistry & Biochemistry, Fairfield University, Fairfield, Connecticut, United States (2) Chemistry, Boston University, Boston, Massachusetts, United States

The amide I vibrational band, in the carbonyl region of the mid-infrared, is known to be diagnostic of protein and peptide secondary structure; helices, sheets, and random coils all exhibit distinct carbonyl-region FT-IR spectra. The sensitivity of the amide I band to secondary structure requires a delocalization of amide I normal modes among several C=O oscillators. We have investigated nearest-neighbor coupling in helical peptides through a combined experimental and computational approach. Our experiments employ isotope-edited FT-IR spectroscopy, where we have strategically enriched specific amide oscillators of a peptide known to adopt a 310 helical structure with C-13. C-13 enrichment shifts the amide I band to frequencies below the broad Amide I envelope, revealing details of inter-amide coupling. We have optimized and performed DFT-based quantum chemical calculations with fixed dihedral angles and C-13 isotopic substitution for identification of amide I normal mode frequencies and delocalized inter-amide coupling constants. Our DFT results were analyzed with Cho's method of Hessian reconstruction in order to calculate DFT-based local mode frequencies and inter-amide coupling constants that give rise to experimentally observed normal modes. Our experimental results have confirmed Cho's ordering of local amide I modes for a peptide of five amide oscillators. We have investigated the relationship between different helical geometries and inter-amide coupling.

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CHED 311

DFT calculations and FT-IR observations of the amide I band of isotopologues of the short helical peptide Z-Aib6-β-Ala-OMe

Jesse D. Dickovick1, [email protected], Chase Foster-Spence1, Matthew C. Rotondaro1,2, Matthew A. Kubasik1. (1) Chemistry & Biochemistry, Fairfield University, Fairfield, Connecticut, United States (2) Chemistry, Boston University, Boston, Massachusetts, United States

The amide I vibrational band of proteins and peptides is known to be diagnostic of secondary structure. However, the mechanisms by which amide oscillators conspire to reveal secondary structure through the contours of the amide I band continue to be the subject of intense theoretical and experimental investigation. We have explored the mechanisms of inter-amide coupling using computational and experimental methods. We have performed quantum chemical computations using Density Functional Theory (DFT). These computations have predicted band positions and intensities as well as revealed the coupling between individual amide oscillators. For our poster, the contour(s) of the amide I band(s) of our peptide as determined by DFT calculations will be compared to experimentally-collected FT-IR spectra of various 13C isotopologues of Aib. Our peptides are homo-oligomers of α-aminoisobutryic acid, which is known to form a 310 helix characterized by an i → i + 3 hydrogen-bonding pattern, as opposed to the i → i + 4 hydrogen-bonding pattern of an α-helix. The C-terminal β-Ala residue estabilishes a hydrogen bonding network that includes three contiguious amide groups that are hydrogen-bonded at both the carbonyl and hydrogen ends of the amide functional group (see figure below). Our hypothesis is that these three interior amide functional groups will form a subset of interacting amide oscillators. In addition, using β-Ala as the C-terminus does not bias the peptide to either a left or right handedness. 13C-labelling localizes amide I vibrations to the 13C-enriched site(s) and shifts amide I infrared absorptions to lower energy by approximately 40 cm-1. Our "isotope edited" spectra reveal local vibrational environments of 13C-labelled amide oscillators and indicate the magnitude of inter-amide coupling.

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CHED 312

Supramolecular self-assembly at the solution/solid interface

Samantha R. Schrecke1,2, [email protected], Henry Castillo2, Steven L. Tait2. (1) Chemistry & Biochemistry, Fairfield University, Fairfield, Connecticut, United States (2) Chemistry, Indiana University, Bloomington, Indiana, United States

Supramolecular self-assembly at surfaces is a topic of growing interest for the rational design of functional surface architectures. The design space using organic building blocks is vast and can allow for specific intermolecular contacts and hierarchical interactions. Here, we will present recent results from an NSF-funded Research Experience for Undergraduates project conducted at Indiana University, where high-resolution scanning tunneling microscopy (STM) was used to characterize self-assembled molecular architectures on highly oriented pyrolytic graphite surfaces in solution. When the samples are characterized in solution a dynamic equilibrium exists between the adsorbed 2D packing observed by STM and a solvated phase. These experiments build our understanding of supramolecular ordering in general, and may also lead to the development of functional supramolecular patterning at surfaces.

CHED 313

Synthesis and surface characterization of ionic liquid 1-methyl piperazinium lactate

Jill Harland, [email protected], Yehia Khalifa, Alicia Broderick, John T. Newberg. Chemistry & Biochemistry, University of Delaware, Newark, Delaware, United States

There is increasing interest in piperazine aqueous solutions due to their ability to capture carbon dioxide. This led to the development of piperazine based ionic liquids (ILs). ILs are salts that are liquid at room temperature and have unique properties, such

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as low vapor pressure. Piperazinium ILs show promise as a possible sequestration medium, although few studies currently exist examining their use for carbon dioxide capture. Here we present results of synthesizing and characterizing 1-methly piperazinium lactate (MPL). Several purification methods were employed to purify MPL including distillation, rotary evaporation, extraction methods, and filtration with activated carbon. The purity of MPL was examined using X-ray photoelectron spectroscopy (XPS), a surface analysis technique that is highly sensitive to IL impurities. By combining the worlds of chemical synthesis and physical chemistry, high purity MPL can be obtained for future carbon dioxide absorption studies.

CHED 314

Thermodynamics of fluoride binding in heme proteins

Kimberly Wodzanowski, [email protected], Thomas Nagle, [email protected], Julia Leonard, Christopher Moll, Jose Cerda. Chemistry, Saint Joseph's University , Philadelphia, Pennsylvania, United States

The temperature dependence of fluoride binding was studied in hemoglobin (Hb), myoglobin (Mb), and horseradish peroxidase (HRP) from 10 °C to 55 °C. Thermodynamic properties, such as the enthalpy change and entropy change of fluoride binding, were determined for all three proteins at pH 5 and pH 7. We found that the entropy change of fluoride binding can varied from -12.8 J/K (for Mb at pH 5 and below 45 °C) up to 434 J/K (for Hb at pH 7 and above 45 °C). Concomitantly, enthalpy change for fluoride binding varied from -18.4 kJ/mol to 131 kJ/mol. Our study shows a strong correlation between the entropy and enthalpy of fluoride binding, a thermodynamic phenomenon that has been observed in the past for oxygen binding heme proteins such as Mb and Hb and better known as the entropy-enthalpy compensation. Our results show that the entropy-enthalpy compensation behavior of ligand binding is also present in HRP which is not an oxygen binding protein. These results contribute to the idea that the entropy-enthalpy compensation is a general behavior of proteins due to the solvation of the globin structure upon ligand binding.

CHED 315

Validating reported experimental temperature by examination of displacement parameters in small-molecule crystal structures

Christina Sotelo1, [email protected], Lu Wang1, Amy Sarjeant2. (1) Chemistry and Chemical Biology, Rutgers University, Piscataway, New Jersey, United States (2) Cambridge Crystallographic Data Centre, Piscataway, New Jersey, United States

Atomic displacement parameters indicate the size, shape, and orientation of the atomic motions in a crystal structure. In general structures, as temperature increases, so do the values of relative displacement. This trend can be exploited in order to develop a

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validation strategy for reported experimental temperature of small molecule crystal structure determinations. To assess the viability of this strategy, sets of polymorphic structures obtained from the Cambridge Structural Database (CSD) were analyzed to discern the exact relationship between average displacement parameter size (Ueq) and data collection temperature. Structures were also analyzed with respect to molecular rigidity and atom hybridization to determine the effects of these on average Ueq. An analysis of such trends and a strategy for temperature validation will be presented.

CHED 316

Utilizing the Cambridge Structural Database to analyze water and metal geometric propensities

Meredith Faulkner1, [email protected], Lu Wang1, Paul Sanschagrin2. (1) Chemistry and Chemical Biology, Rutgers University, Piscataway, New Jersey, United States (2) Cambridge Crystallographic Data Centre, Piscataway, New Jersey, United States

The Cambridge Structural Database (CSD) contains over 820,000 organic and organometallic crystallographic structures. This tremendous amount of data can be used as a rich source of information regarding geometric properties in molecular structures. In the CSD, there are over 125,000 hydrate structures. Here we present research to update and extend the earlier work by others to tabulate and analyze the geometric propensities of how water molecules interact with other molecular groups and ions utilizing both the desktop CSD-System software as well as the CSD Python API. In addition to analyzing hydrate interactions, we also examined the over 38,000 structures with at least one alkali and/or alkaline earth metals along similar lines. Both analyses have implications for ligand design and further understanding of the interaction that occur between chemical moieties.

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CHED 317

Understanding the formation and size distribution of porous poly(o-toluidine) microspheres

Jean Hwang, [email protected], David M. Sarno. Chemistry, Physics and Astronomy, Queensborough Community College of CUNY, Bayside, New York, United States

Poly(o-toluidine) (POT), a derivative of polyaniline, belongs to a class of intrinsically conducting polymers having unique electronic and optical properties. We have developed a simple method to prepare highly porous POT microspheres, which may be useful as electroactive microreactors, scaffolds for catalysis, and encapsulants for drug delivery. Briefly, o-toluidine (OT) and ammonium persulfate are rapidly mixed in aqueous acidic solution to obtain granular POT, which is converted into porous spheres upon addition of excess 4 M ammonium hydroxide. FTIR spectra indicate that spherical and granular POT are chemically identical, but that the spheres contain unpolymerized OT. SEM images show that the morphology depends strongly on the concentration of OT and that spheres are not formed in its absence. We propose that the rapid change to an alkaline environment creates a water-in-oil-in-water double emulsion. The spheres are formed when granular POT dissolves in droplets of unreacted OT and the pores are formed by water droplets trapped in the polymer matrix. The spheres are polydisperse in size. Approximately 65% are 1-5 μm in diameter, 20% are 6-10 μm, 5% are > 10 μm, and 10% are < 1 μm. Preliminary SEM images suggest that reducing the amount of granular POT available to dissolve in the OT droplets may inhibit the formation of larger spheres and other non-spherical objects.

CHED 318

Poly(thioether-co-carbonate) composites from a quinic acid derivative and cellulose for the development of tunable materials from natural products

Brooke Versaw, [email protected], Simcha Felder, Lauren Link, Karen L. Wooley. Chemistry, Texas A&M University, College Station, Texas, United States

Recent demand for sustainable commodity plastics has prompted interest in the development of new classes of naturally-derived engineering polymers. The natural product quinic acid is of particular interest as a starting material for these types of polymers. Quinic acid is readily found in coffee, tree bark, and a variety of green vegetables, and it provides an alternative to traditional petroleum-based starting materials. In this presentation, advances toward the conversion of quinic acid into mechanically-tunable crosslinked composite materials, connected via carbonate and thioether linkages and containing cellulose nanocrystals, will be discussed. Quinic acid

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was converted into a trifunctional monomer, tris(alloc)quinic acid (TAQA), in two steps in good yield (71% overall). Poly(thioether-co-carbonate) networks were then fabricated from TAQA and a range of multifunctional thiols by rapid, solvent-free thiol-ene chemistry; these networks afforded a range of thermal and mechanical properties. To expand the versatility of these poly(thioether-co-carbonate)s, composite networks were fabricated via the integration of nanocrystalline cellulose into the uncured resin, followed by photo-initiated thiol-ene crosslinking. The composite networks expanded the range of achievable thermal and mechanical properties, lending the entire system greater capacity to tune these properties towards a desired application. Of further note, these poly(thioether-co-carbonate) networks allow for the rapid production of biocompatible and biodegradable materials suitable for a wide range of applications in industry and biomedicine, including medical implant devices.

CHED 319

Ln3+-mediated self-assembly of a collagen peptide into luminescent banded helical nanoropes

Manman He2, Lang Wang1,2, [email protected], Jianxi Xiao2. (1) Cuiying Honors College, Lanzhou University, Lanzhou, Gansu, China (2) College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, China

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Design of biomimetic peptides to achieve the desired properties of natural collagen has much potential to build functional biomaterials. A collagen-peptide/Ln3 + system has been constructed and self-assembled to form helical nanoropes with adistinct periodic banding pattern characteristic of natural collagen.The fully reversible self-assembly is specifically mediated by lanthanide ions, but not by other commonly used divalent metal ions. Lanthanide ions not only provide an external biocompatible stimulus of the assembly, but also play as a functional unit to endow the assembled materials with easily tunable photoluminescence. To our knowledge, this is the first report of collagen-peptide-based materials with exquisite nanorope structure and excellent photoluminescent features. These novel luminescent nanomaterials may have great potential in cell imaging, medical diagnostics, and luminescent scaffolds for cell cultivation.

A. TEM images of peptide DColD with specified lanthanide ions at a molar ratio of 1:1: a. La3+


b. Eu3+

, and c. Tb3+

with an increased magnification within the inset boxes shown at the bottom

from d to f.

B. Proposed alignments of DColD in the assembly to generate the periodic banding pattern

observed in the Ln3+

-assembled structures.

Scale bar is 100 nm.

CHED 320

PDMS-co-PVMS copolymer synthesis for microfluidic devices

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Arissa N. Baiamonte, [email protected], Baraka S. Lwoya, Julie N. Albert. Chemical and Biomolecular Engineering, Tulane University, New Orleans, Louisiana, United States

Poly (dimethylsiloxane) (PDMS) is the predominant material used for the fabrication of microfluidic devices because it is an easily synthesized, biocompatible, and flexible material that forms a good seal with other surfaces. However, PDMS is chemically inert and therefore difficult to functionalize for targeted applications, it can swell in the presence of organic solvents, and it can contaminate microfluidic solutions with unreacted oligomers. Therefore, the goal of this research was to synthesize random copolymers of PDMS and poly (vinylmethylsiloxane) (PVMS) that retain the benefits of PDMS and can be functionalized easily via thiol-ene click reactions. In the first stage of this work, dichlorodimethylsilane and vinylmethyldichlorosilane were each reacted with water to produce n-membered dimethylsiloxane rings and n-membered vinylmethylsiloxane rings, respectively. Various reaction conditions were explored, and through gas chromatography mass spectrometry (GC-MS) analysis, it has been shown that adding water dropwise to silane results in consistent yields and percentages of each ring size with the eight-membered ring (four siloxane units) comprising approximately 69% of the product. Because the smaller rings are more reactive and thus more favorable for polymerization, they are separated from the rest of the product by distillation. Polymers are synthesized by reacting these rings with potassium hydroxide and heat to form PDMS, PVMS, and PDMS-co-PVMS copolymers. Again, several reactions conditions were tested to determine the reaction kinetics and to relate molecular weight of the polymer or copolymer to reaction time.

CHED 321

Novel block-poly(L-lactide)-block-poly(ε-caprolactone)-block-poly(L-lactide) systems designed to remove small organic pollutants from aqueous environments

Katrina Bernhardt, [email protected], Amy Balija. Chemistry, Fordham University , Bronx, New York, United States

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Pharmaceuticals and personal care products are the sources of significant amounts of pollution in drinking water that cannot be satisfactorily removed by conventional water treatment systems. Recent research has shown that polymers can be used to effectively remove these organic pollutants. Previous research in our group has focused on synthesizing novel biodegradable linear block copolymers with distinct hydrophobic and hydrophilic regions that can be used as encapsulation agents to remove organic pollutants from aqueous environments. In this presentation, research on the synthesis of block-poly(L-lactide)-block-poly(ε-caprolactone)-block-poly(L-lactide) systems and their applications in organic pollutant removal will be discussed. Polymers with different ratios of L-lactide to ε-caprolactone have been prepared. The efficiency of these polymers in removing Rose Bengal, a model of an organic pollutant, from water was determined. The block-poly(L-lactide)-block-poly(ε-caprolactone)-block-poly(L-lactide) systems were found to remove over 80% of the pollutant within 5 s of contact with the aqueous phase. Further polymer composition analysis and alternative pollutant removal efficiency will be discussed.

CHED 322

Photopolymerized 3D hydrogels for PC12 and human neural stem cell engineering

Paul Gehret, [email protected], Michael Palizkar, [email protected], Weili Ma, Won H. Suh. Bioengineering, Temple University, Philadelphia, Pennsylvania, United States

The desire to engineer different types of human cells is at an all-time high as the life expectancy of humans is steadily climbing. The vast majority of human cells, if not all, are effectively impossible to engineer from molecular building blocks and ions. The concept of making organs and tissue, however, is theoretically possible as we have an increased understanding of how stem cells and stem cell-like cells be manipulated in 2D culture systems. In order to aid in the process of generating functional cells from stem cells, our lab is developing polymer-based three-dimensional (3D) hydrogel systems to engineer environments ideal for neural cell differentiations. We have incorporated photopolymerizable functional groups (i.e., methacrylate) into gelatin and hyaluronan to produce artificial microenvironments for certain cells to more effectively differentiate into neurons. A low-power 3D printed photo adapter incorporating an LED light source was engineered to eventually build a portable photopolymerzation device that can function inside the cell incubator. In the presentation, we will show live-cell and fluorescence microscopy results of cells proliferating and differentiating in the as-prepared 3D hydrogel matrix with PC12 cells and/or human neural stem cells.

CHED 323

Science at the Mount!: Activities of the College of Mount Saint Vincent science club

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Gabriela Mendoza, [email protected], Peter Nunez, [email protected], Elisa Ferrara, Brianna Hoyland, Eberh Garcia, Kimberlyn Nkyeh, Pamela K. Kerrigan. Division of Natural Sciences, College of Mount Saint Vincent, Bronx, New York, United States

The College of Mount Saint Vincent chapter strives to expose our fellow students to the exciting world of chemistry. For the fall semester of the 2015/2016 academic year we hosted an ice cream social in order to introduce new science majors to the Division of Natural Sciences. During National Chemistry Week we had our annual periodic table of elements bake sale whose proceeds went to “Extra Life”, a charity that helps children with cancer. During the Mount's Family and Accepted Students Day, we taught kids how to make ghost crystals and bouncy balls using borax. For our St. Patrick’s Day bake sale we sold syringe pens which was a great success. In April we will have our annual “Tie-Dye” event that illustrates how chemistry is used to dye clothes. We will also host a movie night, showcasing how chemistry and technology is used in a particular film. Furthermore, we are hosting the undergraduate program at the MARM 2016 which will take place on our campus in June. We were given an undergraduate programming grant from the ACS to fund this program. All club members will be volunteering as well.

CHED 324

Chemistry Club activities at Monmouth University

Katlynn Muratore, [email protected], Kristen Flynn, Brian Macalush, [email protected], Opeposi Adetunji, [email protected], Gregory A. Moehring. Department of Chemistry and Physics, Monmouth University, Asbury Park, New Jersey, United States

Monmouth University’s Chemistry Club consistently provides educational and professional development to all students who have an interest in the field of chemistry. Throughout each semester, students are exposed to the field of chemistry in various ways that include attending graduate panels, guest speaker seminars and becoming involved with innovative research. We stress the importance of learning about career paths by providing students with opportunities to visit graduate schools and chemical companies. Not only are we focused on developing students professionally, but also the Chemistry Club volunteers each year to help the community, whether it be cleaning up a local park or doing demonstrations at local schools. Students that are involved with the club are also encouraged to become active members in the Student Affiliate Chapter of the American Chemical Society. Monmouth University’s Chemistry Club strives to shape students throughout their journey of becoming young scientists using the wide range of events offered.

CHED 325

Chemistry community at the University of Maryland, Baltimore County

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Gabriella Balaa, [email protected], Natalie Steenrod, Tara S. Carpenter, Stephen Mang. Chemistry and Biochemistry, University Of Maryland, Baltimore County, Frederick, Maryland, United States

Our student chapter of the American Chemical Society at the University of Maryland, Baltimore County unites a diverse group of students interested in the chemical sciences from various areas of all the STEM fields. With 122 active members in our community, we strive to use our different backgrounds to create a diverse set of activities to unite our members and bring our knowledge of chemistry to our campus and the greater community around our university. Our chapter interacts directly with many elementary school-aged children through local schools to foster a growing appreciation for science in the world around them. Our chapter also focuses on raising money for outreach events and traveling to national meetings with fundraisers that reach out to the whole campus. For our members, we host social and networking events to encourage them to connect with one another and increase our sense of community as a group. As a whole, we successfully use our passion for chemistry to bring students together and encourage science in the general public.

CHED 326

On the path to a national recognition

Aleksandar Goranov3, [email protected], Sarah L. Carberry4, Loraine T. Tan5, Thanuka Udumulla2, [email protected], Katerina Djambazova1. (1) Ramapo College, Mahwah, New Jersey, United States (2) Chemistry Department, Ramapo College of New Jersey, Mahwah, New Jersey, United States (3) School of Theoretical and Applied Science, Ramapo College of New Jersey, Mahwah, New Jersey, United States (4) School of Theoretical and Applied Sciences, Ramapo College of New Jersey, Mahwah, New Jersey, United States

Ramapo College of New Jersey is a public liberal arts and professional studies institution, established in 1969, and hosting about 6,000 students, 28 of which are chemistry and 35 biochemistry majors, respectively. Its ACS Student Chapter was established in 1974, and has been promoting chemistry and biochemistry ever since. Over the last several years, the club improved its activities and obtained two certificates of achievements (2010-2011, 2011-2012), five victory awards during chemistry demo contests in New Jersey in the period of 2012-2015, and an Honorable Mention Award for the last academic year (2014-2015). This project will review the expansion of the activities of the club and the path the students have taken to make a small liberal arts college recognized by the American Chemical Society on a national level. Emphasis will be given to the most recent activities and events of the chapter, its awards at the experimental demo contests, the recent promotion of green chemistry, and the participation of its members on local and national ACS meetings and events.

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CHED 327

What's cooking at ECS?

Nikki Heron, [email protected], Nidhal H. Marashi. Chemistry, Essex County College, Holmdel, New Jersey, United States

In 2014, we started our chapter with six members, now we have more than 40 members involved in the innovation of promoting chemistry in our College Community. Within the past two years; our chapter has gone beyond expectation. Just last month the ECS chapter received a certificate of recognition as a National ACS chapter. Our chapter's members have been diligent to reach out to our community by involving our students in "National Chemistry Week", receiving certificate of community service, mentoring elementary & middle school students on "Thomas Edison Day", cleaning Local Parks on "Earth Day", and reaching out to community by sharing thoughts, knowledge, and what's happening locally and across the globe relating to chemistry, environment, and climate changes. Three of our chapter's members received "Chemistry Ambassador Award" recognition and our Chapter Adviser has received two award recognitions for promoting chemistry in our college and the community.

CHED 328

Organic chemistry: Of the people, by the people and for the people

Donna M. Huryn, [email protected]. University of Pittsburgh, Pittsburgh, Pennsylvania, United States

Organic Chemistry, the study of compounds containing carbon, was, in its infancy, limited to those compounds produced by living organisms. As such, it is a discipline of chemistry that is, literally, “of the people.” However, its reach has expanded far beyond that of compounds produced by living organisms to include aspects of petrochemicals, cosmetics, consumer products and pharmaceuticals, among others. Breakthroughs in organic chemistry have contributed to treating, diagnosing and curing diseases; developing novel materials with unprecedented properties; researching renewable energy sources; and increasing crop production. This talk will present examples of the how the field of Organic Chemistry, a discipline of the people, has been taken up by the people, and provides benefits for all people.

CHED 329

Geochemistry and grand challenges: Arsenic contamination, and geological carbon storage

Anastasia Ilgen6, [email protected], William D. Burgos5, Yoko Furukawa10, Young-Shin Jun9, Sebastien N. Kerisit4, James D. Kubicki7, Sang Soo Lee1, Frances N. Smith3, Andrew G. Stack2, Lisa L. Stillings8. (1) Chemical Sciences and Engineering, Argonne

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National Laboratory, Lemont, Illinois, United States (2) 6110, Oak Ridge National Laboratory, Oak Ridge, Tennessee, United States (3) MSIN P7-25, Pacific Northwest National Laboratory, Richland, Washington, United States (4) Pacific Northwest Natl Lab, Richland, Washington, United States (5) Penn State Univ, University Park, Pennsylvania, United States (6) Geochemistry, Sandia National Laboratories, Albuquerque, New Mexico, United States (7) Geosciences, The Pennsylvania State University, State College, Pennsylvania, United States (8) US Geological Survey, Reno, Nevada, United States (9) Energy, Environmental and Chemical Eng., Washington University in St. Louis, Saint Louis, Missouri, United States (10) Office of Naval Research Global, Tokyo, Japan

This presentation will provide an overview of the significant impact geochemistry explorations have on human lives, with a focus on the contributions of environmental geochemistry. We will focus on the two specific examples: (1) research on the origin, and chemical controls on the fate and transport of arsenic in groundwater, and (2) research on the geochemistry of geological carbon storage. Geochemistry Division members actively explore the areas of bio-, microbial, interfacial, isotope, and petroleum geochemistry, through the use of field studies, laboratory experiments, and computational approaches. Geochemistry uses the tools and principles of chemistry to explain elemental distributions and the evolution and movement of matter between solid Earth, oceans, atmosphere, and the biosphere. Geochemists strive to understand the mechanisms that control processes from the atomic scale to the planetary scale, modelling the behavior of major geological systems on Earth and other planets. Geochemical research impacts human lives as it is crucial for mineral resource extraction, energy production, and understanding the human impacts on the environment: climate and water cycle changes, behavior of pollutants, and soil degradation due to intensive agriculture. Geochemists develop remediation methods for contaminated sites, water purification approaches, as well as geo- inspired materials for applications such as solar cells. Acknowledgement: Sandia National Laboratories is a multi-program laboratory managed and operated by Sandia Corporation, a wholly owned subsidiary of Lockheed Martin Corporation, for the U.S. Department of Energy’s National Nuclear Security Administration under contract DE-AC04-94AL85000.

CHED 330

Waste water treatment and microbeads: teaching students to distinguish media myth from scientific reality

Robert Y. Lochhead3, [email protected], Anne G. Marks1, Karen C. Deniakos4, Sarah E. Morgan2. (1) Science Division, Jones County Junior College, Ellisville, Mississippi, United States (2) School of Polymers and High Performance Materials, University of Southern Mississippi, Hattiesburg, Mississippi, United States (3) School of Polymers High Performance Materials, The University of Southern

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Mississippi, Hattiesburg, Mississippi, United States (4) Science Department, West Jones High School, Laurel, Mississippi, United States

The impact on the environment of plastic microbeads is a subject of current concern that climaxed recently with the passage of the Microbeads-Free Waters Act which banned the use of plastic microbeads in cosmetic products. It is a dictum of this law that plastic microbeads evade the filters of waste-water treatment plants (WWTP). In a National Science Foundation sponsored ‘Research Experience for Teachers’ project, we posed the questions: (1) what is the chemical composition of cosmetic microbeads? (2) What happens to microbeads in waste water treatment plants? We toured a WWTP to critically understand the process. The first stage of treatment comprised a settling pond in which solids either floated or sedimented depending on their density relative to water. The outlet pipe for this pond was situated at an intermediate depth. However, scientific literature indicated that microbeads in the Great Lakes and in the marine environment were detected by manta-trawling which ‘netted’ floating particles. This presented an apparent contradiction. How could floating microbeads flow through a WWTP via the partially submerged pipes? We answered this question by constructing a lab-scale model of a WWTP and we observed the movement of introduced fluorescent microbeads. We also observed the effect of surfactants, oils and grease on the model treatment of microbeads. In all cases, the microbeads remained afloat in the primary sedimentation tank. Large water flows did not cause the microbeads to escape to downstream tanks except for a very few microbeads which appeared to escape through imperfect seals at the surface. Our model agrees with literature reports of better than 99.9% containment in real wastewater plants. In a parallel thrust of the project, microbeads were filtered from facial scrub products and identified by microscopy and FTIR. The beads were found to consist of either polyethylene, poly(ethylene terephthalate) [PET], or iron oxide. The iron oxide beads sank and the others floated in water. Extracurricular lesson plans are planned to teach an awareness of waste water treatment to introduce concepts of the ecological impact of consumer goods, the importance and the relative scarcity of clean water, the principles of buoyancy and sedimentation, an introduction to polymer science, and the need for critical thinking to balance understanding of science reported by non-scientific media.

CHED 331

Chemistry of the people, by the people, for the people how chemistry and the law affects people of Earth

Jonathan L. Kennedy1,2, [email protected]. (1) McKee, Voorhees Sease, PLC, Des Moines, Iowa, United States (2) Division of Chemistry and the Law, Des Moines, Iowa, United States

This presentation will address some of the various ways that the intersection of chemistry and the law affects the people of the earth. While Jonathan's expertise is in the areas of intellectual property law, and particularly patent law, Jonathan will be briefly

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addressing the role of chemistry in not only intellectual property but also forensic science and other areas that chemistry intersects the legal world.

CHED 332

Industrial and engineering chemistry - Chemistry that works

Frankie K. Wood-Black, [email protected]. Ag., Science and Engineering, Northern Oklahoma College, Ponca City, Oklahoma, United States

Did you ever stop and think about how that novel discovery in the laboratory really becomes a viable chemical process? Those involved in industrial and engineering chemistry think about this every day. How do you get that process to be efficient? Or, how can that separation be done with less energy? Or, how can we design the process for the environment? These implementation steps are just as critical to the success of a project as the initial discovery. Come and hear how the Industrial and Engineering Division supports making “Chemistry Work.”

CHED 333

Human health research in the Division of Chemical Toxicology

Stephen S. Hecht1, Amanda C. Bryant-Friedrich1, [email protected]. (1) Masonic Cancer Center, University of Minnesota , Minneapolis, Minnesota, United States (1) University of Toledo, Toledo, Ohio, United States

The mission of the Division of Chemical Toxicology and its flagship journal Chemical Research in Toxicology is to advance the understanding of the impact of chemical and biological agents on the health of the people of Earth. The Division, with over 1000 members, was founded in 1996 and features superlative, innovative, intellectually stimulating programming at each Fall ACS meeting. Research among Division members is varied and strongly multidisciplinary ranging from computational and synthetic chemistry to proteomics, adductomics and metabolomics, biochemistry and molecular biology, drug discovery, drug metabolism, bioanalytical chemistry, DNA and protein modification, bioinformatics, and molecular epidemiology. A major theme of the Division’s research is chemical mechanisms of human toxicity and carcinogenicity. Our scientists are widely recognized for their significant contributions to enzymatic mechanisms of metabolism and detoxification of environmental toxicants and carcinogens to which humans are exposed through the diet, polluted air and water, by consumption of various natural products, and by use of tobacco products. Division members have also played key roles in determining mechanisms of lipid biochemistry related to human health, and in the identification and elucidation of mechanisms of DNA and protein interactions of established human carcinogens such as aflatoxins, metals, aristolochic acid, polycyclic aromatic hydrocarbons, and tobacco-specific nitrosamines. Significant studies of idiosyncratic drug reactions such as drug induced liver injury and

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allergic reactions have also been reported by Division members. Nanotoxicology, the toxic effects of particles, and marine toxins are additional areas of intense interest. Thus, by furthering our understanding of chemical mechanisms of toxicity and carcinogenesis by agents to which humans are commonly exposed from both exogenous and endogenous sources, the Division has a powerful positive influence on the health of all the people of Earth.

CHED 334

Graduate course in professional science communication

Ryan C. Fortenberry, [email protected]. Department of Chemistry, Georgia Southern University, Statesboro, Georgia, United States

Georgia Southern University has implemented a required course in Professional Science Communication as part of the Professional Science Master’s Degree. This course has four facets: journalistic writing, technical writing, oral presentation, and public relations. Each of these builds upon the other to develop the chemistry and physics graduate students within the Master’s of Science in Applied Physical Science in novel ways. This approach is unique within science communication education as it aims to implement journalistic-style communication within scientific writing and presentation. This course also teaches the science students how their research and professional work will be utilized by public relations and marketing personnel within a scientific organization for outreach and advertising purposes. This presentation will showcase the pedagogical approach, student outcomes, and qualitative student perceptions of the course. This course is built from a preexisting Science Communication course taught online through Mississippi College since 2011.

CHED 335

Kitchen conversations

Matthew R. Hartings, [email protected]. Chemistry, American University, Gaithersburg, Maryland, United States

Some of the most difficult chemical transformations are carried out every day by people at home in their kitchens. People without any sort of scientific, let alone chemical training, exercise control over some very complicated chemistry while standing in front of a stove. A more complete engagement of non-chemists with the chemical enterprise would be very beneficial for chemists and chemistry, as a whole. However, chemistry is one of those sciences that many people are uninterested in. One reason for this is that there is a very necessary barrier between non-chemists and a chemical research lab. While safety and proficiency are valid concerns, as chemists, we must find effective ways to engage our friends and neighbors with our science. I have personally found that

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discussing cooking and food are effective ways of bridging knowledge gaps and driving interest in modern chemical research. As food and food additives are also topics of scrutiny for people who are skeptical of the chemical enterprise, developing a food-centric communications approach can have benefits outside of just talking about research. In this talk, I will share my experiences communicating chemistry and my observations of people doing amazing chemistry in the kitchen. I will also discuss how cooking and food can be used to drive a greater interest and engagement with the chemical enterprise.

CHED 336

Beyond the page: Journal article as the starting point in chemical communication

Miranda A. Paley2, [email protected], Carolyn R. Bertozzi1, [email protected]. (1) Department of Chemistry, Stanford University, Stanford, California, United States (2) ACS Central Science, Washington, District of Columbia, United States

In 2015, the American Chemical Society launched its first fully open access journal, a prestigious multidisciplinary chemistry journal ACS Central Science. In the last two years, we have positioned the journal as a go-to venue for the broad dissemination of cutting edge knowledge in chemistry and allied fields. Through the use of a combination of research articles written in a general format, and editorial and news content including interviews, featured news articles, and the views of leading scientists we aim to engage many levels of readers. In this presentation, we will discuss our efforts to make the academic journal less intimidating to a broad audience of scientists and non-specialists alike and highlight tips for writing for an audience outside your particular scientific niche. We will also comment on how our successes with press releases, videos, social media, and LiveSlides, help communicate our science further.

CHED 337

Effective chemistry communication in informal environments

David A. Ucko, [email protected]. Museums + more, Washington, District of Columbia, United States

The National Academies of Sciences, Engineering, and Medicine recently released a report designed to help chemists conduct public outreach. Funded by the National Science Foundation, it offers evidence-based communication strategies drawn from informal learning, science communication, and chemistry education research. This talk will present an overview of the report, along with its background. It will highlight why chemists engage in communication; the current state of chemistry communication; evidence-based research on learning and communication; evaluation to refine goals

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and demonstrate effectiveness; and the committee's recommendations. A companion presentation will focus on details of the framework for the design and implementation of communication activities.

CHED 338

Practical guide to crafting communication strategies to effectively engage the general public

Joseph S. Francisco, [email protected]. Department of Chemistry, University of Nebraska, Lincoln, Nebraska, United States

Chemistry plays a critical role in daily life, impacting areas such as medicine and health, consumer products, energy production, the environment, and many other areas. Despite the growing body of evidence, which indicates that the general public is engaging with science, there is a general perception among those in the field that chemistry is decreasing in popularity and general public interest. As institutions and organization mobilize to invest in efforts to raise public awareness of the importance of chemistry in everyday life, what are effective strategies for designing communication activities? Over the years, many approaches have been tried; some have worked and

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many have failed. As a consequence the chemistry community has lacked a cohesive, evidence-based guide for designing effective communication activities. This talk will outline a framework of five recommended steps, for the design of chemistry communication activities. The key areas of evidence research that supports such a strategy is be presented.

CHED 339

Development of a manufacturing route for MK-8931

William Morris, [email protected]. Process Chemistry, Merck Research Laboratories, Rahway, New Jersey, United States

Alzheimer’s disease (AD) is a neurodegenerative disorder that results in gradual loss of memory and impairment of vocal and motor control before ultimately resulting in death. It is estimated that by 2030 approximately 75 million individuals worldwide will be suffering from AD, a number that represents a 60% increase from the number of people living with the disease in 2015. To address this unmet medical need, Merck has advanced MK-8931, an investigational β-amyloid precursor protein site-cleaving enzyme (BACE) inhibitor, into Phase III clinical trials for the treatment of AD. The evolution of the synthetic route to support the preclinical and clinical development of MK-8931 will be described, including our most recent advances to address the process development challenges observed in earlier synthetic approaches to MK-8931.

CHED 340

Synthesis design through the lens of flow chemistry - How, when, and why

Timothy F. Jamison, [email protected]. Chemistry/18-590, MIT, Cambridge, Massachusetts, United States

Flow chemistry has the potential to revolutionize the synthesis of organic molecules - operationally and conceptually. Flow systems can reduce reaction times, increase efficiency, and obviate problems often encountered in scaling up. In addition to these important practical advantages, flow chemistry expands the “toolbox” of organic reactions available to scientists engaged in the synthesis of molecules – from small-scale experiments to large-scale production. These benefits are a direct result of several features of flow synthesis that batch synthesis typically cannot achieve, for example, the ability to control fluid flow precisely, the access to temperature and pressure regimes not usually considered to be practical, and the enhanced safety characteristics of flow chemical systems. In this lecture we will discuss some of our investigations in this area in the form of case studies, wherein a specific target or family of organic molecules has served as an inspiration for the development of new methods of organic synthesis in flow. The primary thesis we will discuss is that the collection of innovations in flow chemistry has changed the way we consider building molecules. That is, it is both a technological and conceptual advance in chemical synthesis.

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CHED 341

Intercepting and delineating bacterial communication pathways using synthetic ligands

Michael A. Welsh, Joseph D. Moore, Michelle E. Boursier, Tian Yang, Matthew C. O'Reilly, Kayleigh E. Nyffeler, Joseph K. Vasquez, Helen E. Blackwell, [email protected]. Chemistry, University of Wisconsin-Madison, Madison, Wisconsin, United States

Bacteria can utilize chemical signals to coordinate the expression of group-beneficial behaviors in a mode of cell-cell communication called quorum sensing (QS). Once a quorate population of bacteria is achieved in a given environment, bacteria will work together as a group to initiate behaviors that are impossible as individual cells. The discovery that QS controls the production of virulence factors and biofilm formation in many common human pathogens has driven an explosion of research aimed at both deepening our basic understanding of these regulatory networks and developing chemical agents that can modulate QS signaling. The inherently chemical nature of QS makes studying these pathways with small molecule tools a complementary approach to traditional microbiology techniques. In fact, chemical tools are beginning to yield new insights into QS regulation and provide new strategies to inhibit QS. In this presentation, we will outline our general research approach to the design of synthetic ligands capable of blocking or activating QS in a range of Gram-negative and Gram-positive bacteria. Recent examples of how we have used these ligands to reveal new knowledge of QS biology will be highlighted. We will also detail outstanding challenges in the field and suggest strategies to overcome these issues.

CHED 342

From quantum chemistry to drug discovery: the evolution of Schrodinger, Inc. in the world of computational chemistry

Richard A. Friesner, [email protected]. Columbia Univ, New York, New York, United States

We will discuss the evolution of Schrodinger, Inc. from a small company distributing a single quantum chemistry program to its current status as a comprehensive provider of computational chemistry solutions, and a collaborative participant in drug discovery projects. Major challenges in scientific development, software engineering, business strategy and execution, and fundraising had to be overcome in order to successfully grow the company to its present size of 280 employees, including more than 100 Ph. D. computational scientists. A major headwind to success was the disappointment in industry with the efficacy of physics based simulation throughout the 1980’s and 1990’s. The increasing power of computational hardware (in particular GPUs), combined with more mature algorithms and computational models, is now revolutionizing the field, to the point where many pharmaceutical and biotechnology companies are considering a

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major investment in biomolecular simulation. This strategic inflection point is creating many exciting opportunities for Schrodinger and other developers, including academic groups.

CHED 343

Expanding chemical biology with genetic code expansion

Ryan A. Mehl, [email protected]. Dept Biochemistry Biophysics, Oregon State University, Corvallis, Oregon, United States

How would you like to tune the reactivity of your protein? Genetically encoded, site-specific incorporation of non-canonical amino acids (ncAAs) provides unprecedented molecular control over proteins and provides access to countless creative chemical biology applications. Genetic Code Expansion requires that a cell’s translational machinery be expanded to include new orthogonal tRNA/tRNA-synthetase pairs specific for new ncAAs. The challenges in reengineering translation and applying this powerful technology for new chemical biology users will be discussed. The mission of the Unnatural Protein Facility at Oregon State University is to assist in training new users and providing access to new chemical biology tools The UP Facility workshops and conference on Genetic Code Expansion will also be discussed

CHED 344

Crystallography in the undergraduate setting: From diffractometer acquisition to publishing structures in collaboration with undergraduates

Joseph Tanski, [email protected]. Chemistry, Vassar College, Poughkeepsie, New York, United States

As scientific educators, it is important to mentor students in using state-of-the-art instrumentation and in the communication of new knowledge. Just as chemical crystallography can be a fast, effective tool to experimentally observe the structure of molecules and enhance students learning of molecular structure, it can also provide an inspiring opportunity for students to write short, scientific journal style reports that can be edited and published in collaboration with a crystallographer. This talk will focus on strategies for writing a successful grant to obtain a single crystal X-ray diffractometer and a teaching module used to expose undergraduate students to small molecule crystallography including the publication of the resulting crystal structures. With examples of student obtained structures, topics will include: how to justify diffractometer acquisition at a primarily undergraduate institution to funding agencies, sample choice, how the discovery based molecular structure determination lab module works, guiding students in the assessment of molecular packing and intermolecular interactions such as hydrogen bonding, π-stacking, halogen-halogen interactions, and C-H...X (X = O, N, halogen) interactions, and the writing of descriptions of crystal and molecular structures for publication in collaboration with undergraduate students.

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This work was supported by grants from the U.S. National Science Foundation, No. 0521237 & 0911324.

CHED 345

Teaching chemical crystallography without a diffractometer

Arun T. Royappa, [email protected]. Univ of West Florida, Pensacola, Florida, United States

Since most of what we know about molecular structure comes from crystallography, and because it is becoming increasingly important in all branches of chemistry, it is clear that crystallography needs to be a part of the undergraduate chemistry curriculum. However, most chemistry departments do not have the luxury of owning a single-crystal X-ray diffractometer. This is especially likely to be true at a Primarily Undergraduate Institution (PUI). It is nonetheless possible to teach the basics of chemical crystallography using the Cambridge Structural Database (CSD). We demonstrate how this can be done with two free software tools available from the Cambridge Crystallographic Data Centre, WebCSD and Mercury, paying particular attention to the free teaching subset of the CSD. Our approach, a three-hour dry lab exercise involving these tools, has been implemented and used successfully at the University of West Florida, a PUI, for several years. Assessment data for the exercise will also be presented.

CHED 346

Protein crystallography as a research and teaching tool: X-ray crystallography makes a comeback at Bryn Mawr College

Yan Kung, [email protected]. Chemistry, Bryn Mawr College, Bryn Mawr, Pennsylvania, United States

Research and teaching in protein crystallography has expanded immensely in recent years at Bryn Mawr College, a primarily undergraduate liberal arts college in metropolitan Philadelphia. The college's unique composition, with women undergraduates and a small coeducational graduate program, in addition to institutional professional support, regional collaborations, and new developments in our biochemistry curriculum have enabled a dramatic expansion of protein crystallography research as well as deep integration of structural concepts in the curriculum. An overview of the rich history of X-ray crystallography at Bryn Mawr will be presented, followed by a discussion of how recent curricular changes, research grants, and collaborations and partnerships have triggered a resurgence of crystallography in research and teaching at Bryn Mawr. Current limitations and outstanding challenges will also be presented to explore what the future may hold for the incorporation of protein crystallography in a primarily undergraduate setting.

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CHED 347

X-ray crystallography in a directed-inquiry organic chemistry laboratory experiment: Endo versus exo revealed

Jane E. Wissinger1, [email protected], Giang T. Hoang2, Victor G. Young1, Tomohiro Kubo3. (1) Chemistry, University of Minnesota, Plymouth, Minnesota, United States (2) Chemistry, National University of Singapore, Singapore, Singapore (3) Chemistry, University of Florida, Gainsville, Florida, United States

An introductory organic chemistry laboratory experiment was developed which highlights the utility of single crystal X-ray crystallography for structure elucidation. Students perform a reaction sequence involving the synthesis of 2,3,4,5-tetraphenylcyclopenta-2,4-dien-1-one via an aldol condensation reaction followed by the Diels-Alder reaction with styrene. Students are presented with three possible products, the endo and exo diastereomers, and the decarbonylated product. They set out to characterize their beautiful crystalline product by IR and 1H NMR techniques and discover that the stereochemistry of the Diels-Alder adduct cannot be unambiguously assigned, even using the 1H NMR Karplus coupling constants relationships. Students are then given the link to the Cambridge Crystallographic Data Centre and the CIF (crystallographic information file) corresponding to their isolated product for visualization of its three-dimensional structure. The power of single X-ray diffraction for providing bond lengths, bond, angles, and conformations is implicit when students are prompted to explore various aspects of the data. The technique and vast utility of X-ray crystallography is shared with students through an introductory handout and lecture presentation. Student surveys show an appreciation for X-ray crystallography’s role in advancing many fields of science, particularly connecting with biological applications.

Solving the puzzle with X-ray crystallographic analysis

CHED 348

Promoting student success via crystallographic data in the sophomore organic course setting

Kraig A. Wheeler, kaw[email protected]. Eastern Illinois University , Charleston, Illinois, United States

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Many course themes embraced in sophomore organic chemistry reap the benefit of crystallographic data from previous studies. These topics are far-reaching and contribute to many fundamental content areas such as covalent and non-covalent interactions, reaction mechanisms, and conformational preferences. While the importance of crystallography to our understanding of a variety of organic chemistry concepts is undeniable, there often exists a significant disconnect with how the instruction of crystal structure data is treated in the lecture and laboratory setting. This presentation builds on the learning principle that well-placed discussions and experiments that combine the advantages of crystallographic data and traditional approaches help students gain a more lucid grasp of course material. Several lecture and laboratory examples that highlight the benefits and effective use of crystallographic data will be discussed.

CHED 349

Combining X-ray crystallography and computational chemistry with nuclear magnetic resonance spectroscopy for small molecule structural characterization

Jordan D. Zehr, Christian Hamann, [email protected]. Department of Chemistry & Biochemistry, Albright College, Reading, Pennsylvania, United States

Undergraduate students routinely utilize a wide range of spectroscopies (e.g., NMR, IR, UV-vis, Raman) and mass spectrometry to characterize commercially-available compounds as well as products from reactions they perform in the laboratory. In increasing numbers, students are complementing the more common methods of analysis with X-ray crystallography and computational chemistry. We report the intentional combination of three powerful techniques – X-ray crystallography, computational chemistry, and NMR spectroscopy – as a means to more thoroughly interrogate molecular structure, particularly as students come to appreciate that there can be differences between the solid phase, gas phase, and dilute-solution phase structures of molecules. We are investigating a series of sterically crowded products from an electrophilic aromatic substitution discovery experiment performed in our organic chemistry laboratory. Students typically predict that the methoxy functional groups in these molecules are in the plane of the parent benzene ring due to conjugation. They are surprised to learn that X-ray crystallographic analysis reveals the methoxy groups to be out of the plane by varying degrees, depending on the size of the alkyl substituents also attached to the ring. By comparing experimental X-ray crystallographic structures with calculated gas phase structures, students begin to develop an appreciation for the effects of crystal packing forces and how these forces can overcome the structural stabilization predicted by the maximum p-orbital overlap of the in-plane methoxy groups. In addition to providing an estimate of the energies involved in this structural distortion, computational techniques can be used to probe the difference between the X-ray crystal structures and dilute-solution NMR structures: students can compare predicted chemical shifts for the conformers found in the crystal structures with predicted (and actual) chemical shifts for the conformers observed in dilute solution. In summary, students are promoted to a more thorough investigation of

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small molecule structure using X-ray crystallography, computational chemistry, and NMR spectroscopy in combination because they give due consideration to the physical state required for each method of analysis.

CHED 350

Chemical crystallography: how much of it is suitable for an undergraduate class?

Alexander Y. Nazarenko, [email protected]. Buffalo State Coll, Buffalo, New York, United States

Classic courses of crystallography are oriented mostly at graduate students and at very advanced undergraduate students. They always include material that requires good knowledge of advanced mathematics plus good understanding of quantum physics. All this is essential for a crystallographer but is out of reach of most undergraduate chemistry students. At the same time, little attention is paid to chemical aspects of crystals. Here we suggest a multi-step approach to teaching chemical crystallography at undergraduate level: a) Quick 15 min demonstration of crystal structure determination in freshman and sophomore classes (General Chemistry, and analytical chemistry labs). b) More advanced demonstration for junior classes can include study of several samples. After a short introduction and demonstration, students are encouraged to mount and run the data collection themselves using preset experimental conditions. c) For senior elective classes (inorganic chemistry laboratory, advanced organic chemistry laboratory, analytical toxicology, and similar) students synthesize or isolate compounds of interest, obtain suitable crystals, collect and process data, and obtain their ‘own’ crystal structure. Crystalline compounds suitable for these experiments and their sources as well as possible challenges will be discussed. Finally, the full one-semester elective class on structural chemistry is suggested. This class starts with a tutorial-level reminder about point groups and space groups which uses the already known material from inorganic chemistry. Next, a brief introduction to single crystal and powder diffraction is given. A series of laboratory experiments include quick data collection and, most important, data analysis for molecular crystals (polyaromatic hydrocarbons), crystals with known network of hydrogen bonds (sugars), ionic crystals (various salts), zwitter-ions (taurine, amino acids), and/or metalorganic compounds. Fast data collection and processing leaves sufficient time to analyze molecular structure and intermolecular interactions after each experiment. Additional examples include Cambridge Structure Database searches and their analyses. In the end of this class, we prefer to have a full crystal structure determination report in lieu of any sort of exam. Above mentioned approaches were tested in 2013-2016 in various classes at SUNY College at Buffalo.

CHED 351

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Education from 824,520 crystal structures

Amy Sarjeant2, [email protected], Peter A. Wood3, Suzanna Ward1, Colin Groom1. (1) CCDC, Cambridge, United Kingdom (2) Cambridge Crystallographic Data Centre, Piscataway, New Jersey, United States (3) Cambridge Crystallographic Data Centre, Cambridge, United Kingdom

Most of what we know about chemistry comes from three-dimensional structural determinations. However, when teaching chemistry, we rarely focus on the best method for determining molecular structure in the solid state – X-ray Crystallography. The Cambridge Structural Database (CSD) comprises over 800,000 small molecule crystal structures, curated and maintained by the Cambridge Crystallographic Data Centre (CCDC). While the CSD has become the go-to resource for structural chemists, worldwide, it can also serve as a premiere educational resource. In addition to providing three dimensional structure of entries the CSD contains a wealth of statistical information about symmetry, packing, coordination environments, bond distributions, and intermolecular interactions. By choosing our examples well, we can illustrate a huge variety of chemical and crystallographic principles using the information contained in the CSD. This talk will focus on the ways educators can use crystal structure data in the classroom to augment the learning experiences of students.

CHED 352

People of the division of agricultural and food chemistry

Kathryn D. Deibler7, [email protected], Michael Appell5, Michael H. Tunick3, Navindra P. Seeram6, Bosoon Park4, Michael J. Morello1, Charles J. Brine2. (1) PepsiCo Global RD, Barrington, Illinois, United States (2) Princeton ChitoCare, LLc, Princeton, New Jersey, United States (3) USDA ARS, Wyndmoor, Pennsylvania, United States (4) USDA, ARS, Athens, Georgia, United States (5) USDA-ARS, Dunlap, Illinois, United States (6) Biomedical and Pharmaceutical Sciences, University of Rhode Island, Charlestown, Rhode Island, United States (7) Consumer Healthcare, Pfizer, Richmond, Virginia, United States

The Division of Agricultural and Food Chemistry (AGFD) of the American Chemical Society brings together persons particularly interested in the chemistry of agricultural and food products, both raw and finished; to foster programs of general papers and symposia on special topics dealing with this field of chemistry; to promote such other activities as will stimulate activity in and emphasize the importance of research in agricultural and food chemistry. The Division offers a diversity of opportunities for involvement and recognition. History and activities will be discussed.

CHED 353

Making chemistry data infrastructure awesome: The CINF multiplier

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Erin Davis1, [email protected], Elsa Alvaro2. (1) Cambridge Crystallographic Data Centre, Piscataway, New Jersey, United States (2) Northwestern University, Evanston, Illinois, United States

The digital age has brought the world of chemistry the ability to accumulate and transfer a tremendous wealth of information. The challenge is that there IS now a tremendous wealth of information. How do people store and find data? How do people learn from this overwhelming volume of data? How do we extract trends and new knowledge from this information? How do we manage standards and formats in order to extract trends and new knowledge? The questions that chemical information brings up are as numerous as those it answers. In this talk, we explore how the Division of Chemical Information connects a diversity of chemistry professionals across the enterprise to address these challenges: exploring how chemical information is created, stored, managed, accessed, and learned from - in support of and applicable to all avenues of chemistry research, education, and utilization.

CHED 354

Polymers all around us - The POLY road show

Frank D. Blum, [email protected]. Chemistry, Oklahoma State University, Stillwater, Oklahoma, United States

Polymers are all around us. They are the materials for the people and, usualy, by the people. Their discovery, development and use will be told in a serices of snippets. The "POLY Road Show" has several examples from the history of polymers. In the end, we conclude that we are indeed in the Polymer Age.

CHED 355

Biological chemistry for the people

Yi Tang, [email protected]. Department of Chemistry and Biochemistry, UCLA, Los Angeles, California, United States

The BIOL division focuses on understanding the fundamental mechanisms of biological phenomena, covering (among others) structure, function, and regulation of biologically active molecules; gene structure and expression; biochemical mechanisms; protein biosynthesis; protein folding; membrane structure-function relationships; bioenergetics; and immunochemistry. Research by members of the division, from both academic and industry, have (among others) revealed the molecular basis of diseases, led to the development of life-saving pharmaceuticals, and enabled the application of biological tools to improve the everyday lives of people in the world. In this presentation, an overview of the BIOL division activities and recent discoveries pertaining to the central theme of the meeting, “Chemistry of the People, by the People, for the People" will be presented.

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CHED 356

New generation chemistry for newborn screening of inborn errors of metabolism

Frantisek Turecek1, [email protected], Michael H. Gelb2, C. Ronald Scott1. (1) Univ of Washington, Seattle, Washington, United States (2) Dept of Chem 36 Bagley Hall, Univ of Washington, Seattle, Washington, United States

The combination of synthetic organic chemistry with modern analytical methods such as tandem mass spectrometry has been developed into a powerful tool in clinical diagnostics of metabolic disorders. In particular, lysosomal storage disorders (LSD) represent a group of over 40 metabolic diseases caused by deficient enzymes specializing in catabolic degradation of lipids, saccharides, proteins and their conjugates such as glycolipids and lipoproteins. LSD are rare disorders that do not present in affected children at birth and are difficult to diagnose before organ or systemic damage sets in. In the last decade, sophisticated treatments based on enzyme replacement or erythropoietic stem cell transplantation therapies have been developed for several LSD that stressed the need for an early detection of affected newborns by large scale screening. Our team has been developing diagnostic methods utilizing synthetic enzyme substrates and product quantitation by tandem mass spectrometry (MS/MS). The MS/MS methods are suitable for large-scale newborn screening of entire newborn populations, e.g., >1,500,000 newborns in New York state and >150,000 newborns in Washington state. The lecture will describe the new chemistry of assays for enzymes responsible for deficient sphingolipid degradation, mucopolysaccharidoses, and neuronal ceroid lipofuscinoses. These assays have been tailored for bioanalytical work with dried blood spots and are compatible with the workflow in state newborn screening centers. The new methods allow massive multiplexing of quantitative analyses by tandem mass spectrometry.

CHED 357

Green gasoline: A better biofuel

John R. Regalbuto, [email protected]. Department of Chemical Engineering, University of South Carolina, Columbia, South Carolina, United States

In this election year, the issue of alternate transportation fuels has often surfaced. There is currently a significant amount of confusion regarding the potential fuel economy of ethanol-fueled vehicles in claims that the higher octane of ethanol permits engine operation at higher compression ratios, and the resulting higher engine efficiency will compensate for lower energy density to ultimately give higher fuel economy than gasoline in the modified engine. In this paper a simple thermodynamic analysis, validated by experimental data from the literature, is used to show that increased thermal efficiency of ethanol engines at higher compression ratios will not nearly compensate for the large difference in energy density

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vis-à-vis gasoline. The key is to understand that thermal efficiency and fuel economy are not the same thing; fuel economy is the product of energy density and thermal efficiency, and energy density dominates. The talk will conclude with a roadmap showing the catalytic and biocatalytic routes to biohydrocarbon fuels from non-food lignocellulosic feedstocks such as agricultural and forest waste and energy crops such as switchgrass

CHED 358

Making the bones of chemistry visible

Michelle M. Francl1,2, [email protected]. (1) Dept of Chem, Bryn Mawr Coll, Bryn Mawr, Pennsylvania, United States (2) Vatican Observatory, Rome, Holy See [Vatican City State]

Over a century ago Nobel prize winning chemist Wilhelm Ostwald urged teachers of chemistry to keep “the bony skeleton of the chemical body” visible through the facts. Whether communicating chemistry to the general public or to beginning students, the facts are often not enough. Chemists need to help novices learn to use chemical information to grapple with novel questions that matter to them. I will propose a simple conceptual framework to help non-chemists develop a chemical imagination, able to make predictions and decisions as chemists might, to see through to the atoms and molecules that make up the world around them.

CHED 359

Teaching students how to communicate chemistry

Holly C. Gaede, [email protected]. Chemistry, Texas A&M University, College Station, Texas, United States

Communication skills are of paramount importance to chemistry majors, no matter their ultimate pursuits. Nonetheless, students are often reluctant to embrace this reality, and curricula can be deficient in teaching and developing these skills. I will discuss the evolution of our senior seminar course, in which chemistry students prepare several oral and written assignments sourced from recent chemical literature. Student success is improved by providing detailed motivation for every assignment and explicitly teaching even basic skills like how to read a scientific paper. Practice and feedback are essential in developing student competence, and furthermore, students can be desensitized to public speaking fears by talking frequently in low-pressure situations. Finally, students gain scientific insight when asked to write and speak for a general audience.

CHED 360

On the nature of chemistry publishing

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Stuart Cantrill, [email protected]. Nature Chemisty, London, United Kingdom

The basic unit of scientific publishing — a paper — has not really altered all that much for hundreds of years, but now that we have the internet, shouldn't this be changing? This talk will look at different aspects of communicating chemistry in the modern (and more connected) world — through traditional methods such as journals (and all that entails, including a behind-the-scenes look at Nature Chemistry’s editorial processes), but also using ‘new’ media such as blogs and Twitter. Since launching in 2009, Nature Chemistry has engaged significantly with the chemistry community through these more informal outlets, showcasing a range of bloggers in the Blogroll column featured in the journal as well as actively using Twitter to interact with our followers (rather than simply as a one-way channel to promote our own content). In many cases these interactions have led to productive conversations that have occasionally resulted in commissioned content for the journal, some examples of which will be highlighted in this talk.

CHED 361

How to talk to a reporter about your science

Lauren Wolf, [email protected]. American Chemical Society, Washington, District of Columbia, United States

Scientists, particularly chemists, are detail-oriented people. They measure their reagents precisely, they report their reaction dynamics to the femtosecond, and they usually caveat the potential impact of their research out the wazoo. So it’s no surprise that many chemists shy away from talking to the press. They worry that all that detail will be stripped out their work and reduced to misinformation. But talking to the press is important if chemists want to communicate with the public about why their work, and chemistry in general, is important. So what’s an overly cautious chemist to do? My talk will discuss how to navigate the relationship between scientist and reporter in order to inform the public clearly and accurately about why your chemistry rocks.

CHED 362

Tell it slant

Deborah Blum, [email protected]. Knight Science Journalism, Massachusetts Institute of Technology, Cambridge, Massachusetts, United States

The poet Emily Dickinson once wrote: “Tell all the truth but tell it slant/Success in Circuit Lies/Too Bright for our infirm Delight/The Truth’s superb surprise.” In this presentation, I’ll look at the way science writers, like myself, employ narrative story telling techniques in order to show members of the general public that - contrary to what they learned in high school - chemistry is both fundamental to their daily lives and fascinating. I’ll include the way I’ve told both true crime and public health stories in making this case

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CHED 363

3D Printing molecular prosthetics

Martin D. Burke, [email protected]. Univ Illinois Urbana Champaign, Urbana, Illinois, United States

The talk will describe recent efforts to create a 3D printer for molecules that enables the development of prostheses on the molecular scale (and many other types of small molecules that perform high-impacting functions).

CHED 364

Supramolecular soft materials for energy and medicine

Samuel I. Stupp, [email protected]. Northwestern University, Evanston, Illinois, United States

Supramolecular materials have the potential to mimic the structures and dynamics of biological systems, and it is therefore a rich platform for the development of bio-inspired materials. The interesting features of supramolecular soft materials include, nanoscale control of dynamics, highly responsive behavior to external stimuli, capacity to self-heal defects, noncovalent co-localization of functional domains, and the use of self-assembly to optimize function, among many others. The development of these materials poses a great challenge to chemists since it requires the integration of many fields including synthetic organic chemistry, supramolecular chemistry, materials science, physical chemistry, and computational chemistry, among others. This lecture will describe supramolecular soft materials that mimic the photosynthetic machinery in biological systems by integrating the necessary functions to generate solar fuels. As a second topic, the lecture will discuss the development of bioactive supramolecular materials for biomedical targets such as regenerative medicine and the development of targeted therapies.

CHED 365

Design of materials for organic light-emitting diode displays

Nora S. Radu, [email protected], Gene Rossi, Frederick Gentry, Norman Herron, Tiffany N. Hoerter. DuPont, Wilmington, Delaware, United States

Organic light emitting diode (OLED) technology enables for more vivid color, higher contrast, faster response, thinner panels, a wider viewing angle and lower power consumption than traditional liquid crystal displays. We will present our recent progress in designing small molecule and polymeric materials that will enable display manufacturers to deliver superior OLED device performance with lower manufacturing costs for large-format displays.

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CHED 366

3D Printing of flexible electronics and sensors

Jennifer A. Lewis, [email protected]. School of Applied Sciences and Engineering, Harvard University, Cambridge, Massachusetts, United States

The ability to pattern functional materials in planar and three-dimensional forms is of critical importance for several emerging applications. We have developed a multimaterial 3D printing platform that enables the rapid design and fabrication of soft functional devices in arbitrary shapes without the need for expensive tooling, dies, or lithographic masks. In this talk, I will describe our recent efforts to create soft electronics and sensors for applications ranging from wearable devices to intelligent biochips.

CHED 367

Authentic research in introductory chemistry laboratory course

Julianne Vernon1, juliever@umich.edu, John P. Wolfe2, Deborah Goldberg1. (1) Ecology & Evolutionary Biology, University of Michigan, Ann Arbor, Michigan, United States (2) Chemistry, University Of Michigan, Ann Arbor, Michigan, United States

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Given that early research experiences tend to increase persistence in STEM, it is important to develop models to scale up the number of students who have such experiences. This work describes the implementation of faculty-led research projects in the introductory chemistry laboratory course. Two research streams, snow chemistry and solar cell technology, were offered for the first time last fall. Pre and post survey instruments were given to the research sections as well as to the control group, non-research sections. The survey focused on students’ persistence in STEM, self-efficacy in chemistry, and interest in conducting research. Focus groups were conducted as well to gain better insights into students’ experience in the research sections.

CHED 368

Updating the organic laboratory curriculum: Modification of classical lab experiments through the incorporation of technology and techniques used in the contemporary research environment

Robert G. Aslanian, [email protected]. Chemistry, New Jersey City University, Jersey City, New Jersey, United States

The practice of organic chemistry is changing due to advances in synthetic methodology and technology. In order to provide our students with a skillset that is pertinent to the needs of academics and industry, and thus make them more competitive, curricula must be evaluated and updated to deliver relevant knowledge and experience. We undertook a redesign of two classic organic reactions, the Diels-Alder reaction and the Fisher esterification, with the goal to provide a laboratory experience that would mirror the types of approaches a chemist in the real world would take to running these reactions. Both reactions were modified by the introduction of the modern concept of green chemistry, use of microwave synthesis and in the case of the Fisher esterification, gas chromatographic analysis. This presentation will disclose some of the new experiments we have developed to meet this goal.

CHED 369

Transforming the organic lab experience: Implementation and evaluation of an organic lab module curriculum at a four-year institution

Tina G. Goudreau Collison2, [email protected], Jeremy A. Cody3, [email protected], Thomas D. Kim1, Brian L. Edelbach4, Jason P. Anderson4, William Marmor2, Rodgers Kipsang2. (1) Dept of Chemistry, Rochester Inst of Tech, Rochester, New York, United States (2) Rochester Inst of Technology, Rochester, New York, United States (3) School of Chemistry and Materials Science, Rochester Inst of Technology, Rochester, New York, United States (4) Chemistry, Monroe Community College, Rochester, New York, United States

This work discusses the full implementation of our innovative macroscale organic chemistry lab modules. A description of changing from a traditional expository organic

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chemistry lab curriculum to delivering these novel organic lab modules will be discussed. The results obtained using Reformed Teaching Observational Protocol (RTOP) will be outlined and correlated to the transferability of the modules between different instructors and the transportability of the modules between different institutions. Additionally, preliminary data using the Meaningful Learning in the Lab (MLLI) instrument will be reported.

CHED 370

Why onions make you cry? A GS-MS experiment for undergraduate chemistry laboratory

Yan Sun1, [email protected], Omowunmi A. Sadik3, Alexsandra S. Silva2. (1) Chemistry, SUNY Binghamton, Binghamton, New York, United States (2) Dept of Chemistry, SUNY Binghamton, Binghamton, New York, United States (3) State Univ of New York Suny, Binghamton, New York, United States

An undergraduate laboratory exercise involving GS-MS analysis of onion lachrymatory factor (LF) will be presented. The lachrymatory factor, propanethial S-oxide, is one of the major flavor compounds in onions and can make people “cry” when its vapor comes into contact with eyes. Students extract the LF from different types of onions and quantify their contents using gas chromatography with mass spectrometry detection. This experiment can be adapted for upper-division undergraduate students in analytical chemistry, organic chemistry or biochemistry and can serve as the place where GC-MS can be introduced into the undergraduate curriculum. This exercise teaches students the interpretation of mass spectra, the GS-MS instrumentation, the extraction techniques and the chemistry of enzymatic reactions.

CHED 371

Introducing mini-laboratory projects based on name reactions in organic chemistry for the sophomore organic chemistry laboratory

Renuka N. Manchanayakage, [email protected]. Chem Dept, St. John Fisher College, Rochester, New York, United States

Despite the accepted pedagogical value of integrating research into the laboratory curriculum, this approach has not been widely adopted. There are many challenges to this change, especially in organic chemistry, where a large number of students are required to take the course, special glassware or setups may be needed, and dangerous chemicals and safety are of special concern. At St. John Fisher College, organic chemistry laboratory curriculum has been revamped by incorporating mini-lab projects based on organic chemistry name reactions, in order to foster increased independence and confidence in a laboratory environment. The projects can be incorporated under limited facilities, still giving students a ‘research-like’ experience. After introducing chemistry literature search using SciFinder, a name reaction is

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assigned to each student early in the semester. Students are first required to write an introduction including a literature review of the assigned name reaction. Students are then given a short experimental protocol which they use as the basis for developing their experimental plan which includes the reagents, major techniques, purification and characterization methods and waste disposal procedures. Students have two to three weeks to complete the project and submit a formal laboratory report including an introduction with the literature review, an experimental section, a complete discussion of their results and list of references.

CHED 372

Kinetics and photochemistry of ruthenium bisbipyridine diacetonitrile complexes – An interdisciplinary inorganic and physical chemistry laboratory exercise

Teresa L. Rapp, [email protected], Susan R. Phillips, Ivan J. Dmochowski. Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, United States

The study of ruthenium polypyridyl complexes can be widely applied across disciplines in the undergraduate curriculum. Ruthenium photochemistry has advanced many fields, including dye-sensitized solar cells, photoredox catalysis, light-driven water oxidation, and biological electron transfer. Equally promising are ruthenium polypyridyl complexes that provide a photolabile moiety for transiently ‘caging’ biologically active molecules. Photo-uncaging involves the use of visible light to break one or more bonds between ruthenium and coordinated ligand(s), which can occur on short timescales and in high quantum yields. In this work we developed laboratory exercises employing a model ’caged’ acetonitrile complex, Ru(2,2'-bipyridine)2(acetonitrile)2, or RuMeCN. Students made RuMeCN in an advanced synthesis laboratory course and performed UV-Vis spectroscopy and electrochemistry. The following semester students investigated RuMeCN photolysis kinetics in a physical chemistry laboratory. These two exercises may also be combined to create a 2-week module in an advanced undergraduate laboratory course.

CHED 373

Teaching instrumental analysis with homebuilt as well as commercial instruments

Neil D. Danielson, [email protected]. Chemistry and Biochemistry, Miami University, Oxford, Ohio, United States

There are four major instrumental analysis topics taught in most laboratory courses: molecular spectroscopy, atomic spectroscopy, chromatography, and electrochemistry. However, commercial instruments used to teach these topics can promote the “black box effect” and overemphasize the computer control aspect. We have shown that spectrophotometry and fluorescence can be effectively demonstrated using Lego blocks to align the cuvette with the LED light source and a photodiode detector with a current-

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to-voltage breadboard circuit. Aspects of Beers law such a pathlength using two cuvettes and stray light can be easily taught with the Lego colorimeter. The LED light power can be easily adjusted for Lego colorimetry and Lego fluorimetry showing it is not a factor for the former technique but is critical for sensitivity for the latter technique. One downside is the Lego fluorimeter can only detect ppm levels of quinine but when our students measure that same 0.1 ppm quinine solution on a commercial instrument, the idea that fluorescence is considered a trace technique is made clear. We have designed and characterized two flame emission instruments of differing complexity for teaching instrumental analysis to our chemistry and biochemistry majors. Alkali metals such as potassium in instant breakfast drink can be easily determined by both instruments. However, trace transition metals in this same sample cannot be determined and it is important student gain experience in ICP atomic emission spectroscopy for that analytical problem. Again the contrast between the two instruments provides a vivid learning experience. We teach gas chromatography using a homebuilt instrument assembled from readily commercially available components such as a drink carbonation CO2 tank to provide the carrier gas, a septum based or HPLC valve injection port, a standard 30 m wide-bore capillary column, a consumer convection oven with a thermocouple, and a photoionization detector modified as a flow cell. However, student use of a GC-FID with an autosampler and a GC-MS is also part of this experiment, to demonstrate precise temperature effects and qualitative analysis of unknowns such as auto touch-up paint. Electrochemistry techniques such as potentimetry, cyclic voltammetry, and coulometry tend to be simpler and more easily understood by students. However, we improved the coulometric starch –iodine endpoint precision by using a photodiode and the current-to-voltage circuit for detection.

CHED 374

Medical research volunteer program (MRVP): Innovative program promoting undergraduate research in the medical field

Bilal R. Kaafarani, [email protected], Michael M. Dagher, Jessica A. Atieh, Karl C. Mansour, Marwa K. Soubra, Mariya M. Akkawi, Samia J. Khoury, Hani Tamim. American University of Beirut, Beirut, Lebanon

Most educational institutions lack a structured system that provides undergraduate students with research exposure in the medical field. The objective of this paper is to describe the structure and function of the Medical Research Volunteer Program (MRVP) which was established at the American University of Beirut, Lebanon, as well as to assess the success of the program. The MRVP is a program that targets undergraduate students interested in becoming involved in the field of medical research early on in their academic career. It provides these students with an active experience and the opportunity to learn from and support physicians, clinical researchers, basic science researchers and other health professionals. Through this program, students are assigned to researchers and become part of a research team where they observe and aid on a volunteer basis. This paper discusses the structure and function of the MRVP’s four major pillars: the students, the

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faculty members, the MRVP committee, and the online portal. Moreover, details of the MRVP process are provided. The success of the program was assessed by carrying out analyses using information on MRVP participants (both students and faculty). The MRVP is a program that provides undergraduate students with the opportunity to learn about research firsthand as they volunteer and aid in different research projects. Consequently, faculty members get the help needed to conduct their research and are offered an opportunity to influence future generations. It has been shown that so far the MRVP has been successful in reaching its goals, for both students and faculty.

CHED 375

Analyzing Cu and Pb in pore water in Tokyo Bay, Japan by anodic stripping voltammetry (ASV)

Hidemitsu Katsura1,2, [email protected]. (1) IPROM, Universiti Kuala Lumpur, Kuala Lumpur, Malaysia (2) TOKYO UNIVERSITY OF MARINE SCIENCE & TECHNOLOGY ( FORMER TOKYO UNIVERSITY OF FISHERIES), Tokyo, Japan

Generally free heavy metal ions are poisonous to biological actives. However we have been known that if heavy metal ions are complex formation, toxicity is decreasing to biological activities. Meanwhile existing state of heavy metal ions is very important to geochemical behaviour. Thus it is very important to investigate existing state of heavy metal ions in sea water and pore water in sediments of the bottom of the sea. Hence the objects of this research were as follows: #1 Developing methods of analysis by Anodic Stripping Voltammetry (ASV) for free heavy metal itons with free ligands. #2 Analyzing concentration of copper, lead and their ligands with existing state in pore water in sediments of the bottom of Tokyo Bay, Japan. #3 Analyzing oxidation reduction potential for these samples. The sediments samplings were taken place in June 1990 in Tokyo Bay, Japan by Smith-McIntyre mud-sampler. After the sampling I took samples of pore water by centrifuge from natural sediments and anthropogenic oxide sediments. I analyzed total concentration of copper and lead, concentration of free ions of copper and lead and concentration of free ligands in these pore water samples with and without anthropogenic infrared ray radiation. The total concentration of copper in pore water from reductive sediments was 60 ppb to 129 ppb, total concentration of lead in pore water from reductive sediments was 4 ppb to 40 ppb and total concentration of free ligands in pore water from reductive sediments was 0.91 micro mol/L to 2.6 micro mol/L.. Meanwhile concentration of free copper ions in pore water from reductive sediments was 29 ppb to 101 ppb. I also analyzed these concentration in pore water from anthropogenic oxidized sediments and results were changed samples from natural sediments. However it did not have any accurate trend.

CHED 376

Leveraging resources on VIPEr to teach inorganic chemistry

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Elizabeth R. Jamieson2, [email protected], Chip Nataro1, [email protected]. (1) Lafayette Colg, Easton, Pennsylvania, United States (2) Ford Hall - Chemistry Dept, Smith College, Northampton, Massachusetts, United States

The Interactive Online Network of Inorganic Chemists (IONiC) has worked to improve teaching and learning in inorganic chemistry for over ten years. The foundation of this community is the Virtual Inorganic Pedagogical Electronic Resource (VIPEr, www.ionicviper.org). With over 900 registered faculty users from around the world, VIPEr is a vibrant community of committed educators who have developed over 700 learning objects (LOs) for use in the classroom. This talk will highlight the ways that faculty can use the IONiC network and VIPEr resources to incorporate current research and active learning strategies in their inorganic chemistry course(s). The presenters will discuss how they leverage the community to teach their own inorganic courses and recent innovative ways that people have used VIPEr to crowdsource assessment data, collaboratively develop classroom materials, share what they are doing and incorporate new methods of teaching into their classes. VIPEr: come for the content, stay for the community.

CHED 377

Evolving state of inorganic chemistry at Merrimack College

Anthony L. Fernandez, [email protected]. Merrimack Colg, North Andover, Massachusetts, United States

In several recent articles it has been shown that undergraduate inorganic chemistry courses can vary widely in terms of their topical coverage. Over the past 16 years, the inorganic chemistry curriculum at Merrimack College has undergone significant changes in the topics included in the course, in the laboratory curriculum, and in its location in the typical course sequence followed by chemistry and biochemistry majors. Additionally, the pedagogic approach employed in the course has become much more student-centered over this time. This presentation will focus on how inorganic chemistry has been taught and is currently being taught at Merrimack College. The overall structure of the current course, the student-centered pedagogy, examples of assigned student activities, and the laboratory curriculum will be discussed.

CHED 378

From breadth to depth: An integrated approach to providing depth for students in inorganic chemistry

Alexsandra S. Silva, [email protected], Wayne E. Jones, [email protected], Dongsheng Ji, Yan Sun, Zakiya Skeete, Wei Wu, Anting Chen. Department of Chemistry, State University of New York at Binghamton, Binghamton, New York, United States

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The traditional 1 year inorganic chemistry course is often perceived as a mile wide and an inch deep. Touching on topics including solid state, organometallic, bioinorganic, main group, and others, while not providing depth. We have introduced a one semester breadth course designed to introduce students to all areas of inorganic chemistry and then providing a range of inorganic 2 options. The second semester options provide students the opportunity to select one aspect of inorganic chemistry to which they have been exposed and dig into depth in that topic. In addition, the hands-on experience is an important part of our program. We will discuss the laboratory component of the curriculum. Special attention will be given to Inorganic and Materials Laboratory, a course designed to bridge traditional disciplinary boundaries and to provide research-oriented experiences; we will also describe how independent studies courses enriches the students’ experience in our department.

CHED 379

Metallome chemistry and evolution: A different approach to teaching inorganic chemistry

Alvin L. Crumbliss, [email protected]. Dept of Chem, Duke Univ, Durham, North Carolina, United States

We will present the details of an introductory seminar course based on the metallome (the collection of metals essential to life) and how it interacts with the environment and the other “omes” (proteome, genome and metabolome) on a geological time scale. A systems chemistry approach is used whereby an analysis structure {external pressure – response - emergence – changed entity} is used to explain how environmental changes since the Big Bang influenced element formation and metal ion speciation, and thus bio-availability and bio-utility. That is, how the metallome came to influence the proteome, genome and metabolome, and the evolution of life. This provides an opportunity to teach the chemistry of the representative and transition elements, as well as bioinorganic chemistry. The chemistry of the metallome can serve as a vehicle to teach three major types of equilibrium reactions - solubility, redox and complexation – as well as kinetics, particularly ligand exchange kinetics and catalysis. For example, the Great Oxidation Event 2.3 billion years ago changed metal ion solubility by oxidizing CuS and ZnS to the corresponding sulfates, and iron(II) to iron(III), thus affecting their bio-availability. Microbes adjusted to this change by producing chelators to complex iron(III) and maintain solubility and bio-availability. No text (although introductory chemistry texts are used as reference resources) is used so students learn to read and analyze primary literature from Scientific American to Proceedings of the National Academy of Sciences. This approach presents students with an upfront coherent rationale for studying the principles of inorganic chemistry. An additional benefit of this approach is that students learn how interdisciplinary research is done as the course is centered on the inorganic chemistry bridge between geology and biology.

CHED 380

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Inorganic curriculum for undergraduate students at Yale

Jonathan Parr, [email protected]. Department of Chemistry, Yale Univ, New Haven, Connecticut, United States

The inorganic course offerings for undergraduates at Yale are varied and cover topics in coordination chemistry, bioinorganic and organometallic chemistry as well as green chemistry and alternative energy. The laboratory course includes x-ray diffraction, organometallic synthesis, bioinorganic and homogeneous catalysis, affording students the opportunity to use IR, UV-vis and NMR to characterize their products and investigate their reactions.

CHED 381

Inorganic chemistry at Trinity College

M Parr, [email protected], Ralph O. Moyer. Chemistry, Trinity College, Hartford, Connecticut, United States

Unlike organic chemistry and physical chemistry, the syllabus for a common core in inorganic chemistry appears more divergent and less uniform, partly due to the breadth of the material. The Chemistry Department at Trinity College offers two semesters of inorganic chemistry for chemistry and biochemistry majors who are typically in their junior year. The second semester includes a laboratory component where students can explore the role of magnetic susceptibility, x-ray diffraction and spectroscopic methods for structural characterization of inorganic and organometallic systems. The evolution of the inorganic curriculum at Trinity over the last 40 years is the focus of this presentation.

CHED 382

Advanced inorganic chemistry lecture and laboratory at Fairfield University

John R. Miecznikowski, [email protected]. Fairfield University, Fairfield, Connecticut, United States

Advanced Inorganic Chemistry is an upper-level lecture and laboratory course at Fairfield University for junior and senior chemistry and biochemistry majors and minors. The one-semester lecture and laboratory courses have Physical Chemistry as a co-requisite. The lecture course meets for 150 minutes per week and the laboratory course meets for four hours each week. Students earn three academic credits for the lecture course and two academic credits for the laboratory course. The lecture course introduces students to the interdependence of chemical bonding, spectroscopic characteristics, and reactivity properties of coordination compounds and complexes using the fundamental concept of symmetry. The laboratory course is a synthetic inorganic lab with an emphasis placed on characterization. In the laboratory, students have the opportunity to synthesize, characterize, and investigate the physical and

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reactivity properties of coordination, organometallic, and air-sensitive complexes. In my presentation, I will describe the topics presented in the lecture course and I will describe the laboratory experiments that the students perform. I will also give the student learning outcomes for both the lecture and the laboratory courses. In addition, I will describe some of the instructional methods used in both the lecture and laboratory courses.

CHED 383

Adapting advanced inorganic chemistry lecture and laboratory instruction for a legally blind student

Matthew J. Guberman-Pfeffer 2, [email protected], John R. Miecznikowski1. (1) Fairfield University, Fairfield, Connecticut, United States (2) Department of Chemistry , University of Connecticut, Storrs, Connecticut, United States

To explore and explain chemical phenomena, visual observations and representations are often used in the lecture and laboratory. The translation of conventional chemical drawings and laboratory observations into a ‘language’ that is more accessible to a diversity of students, particularly visually impaired or blind students, is an instructional issue of increasing relevance The American Chemical Society's publication Teaching Chemistry to Students with Disabilities: A Manual for High Schools, Colleges, and Graduate Programs, directs instructors to “Verbally describe or explain…visual information.” However, best practices for how to describe visual concepts or representations (e.g. symmetry properties, character tables, and molecular orbital diagrams), as well as instances when tactile presentations of material are more helpful than verbal explanations, are poorly documented in the literature. The paucity of instructional guidance in particularly acute for advanced chemistry courses. In my presentation, I will discuss content-specific, field-tested strategies and techniques that facilitated my success as a blind student in an advanced inorganic chemistry lecture and laboratory. These approaches attempt to make each step in the logical progression from Lewis structures, to molecular geometries, symmetry operations, point group assignments, and qualitative molecular orbital diagrams intelligible to a visually impaired student. The discussed methods may aid the instruction of other blind, as well as sighted students, by offering an alternative perspective from which instructors can communicate the same material.

CHED 384

Introduction of sustainability topics into the inorganic chemistry laboratory

Marta Guron, [email protected], Jared J. Paul, [email protected]. Department of Chemistry, Villanova University, Villanova, Pennsylvania, United States

At Villanova University, Inorganic Chemistry and the laboratory experience are offered for first-year chemistry majors. Students are introduced to bench-top synthetic

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techniques as well as advanced instrumentation at this stage of their chemistry careers with the idea of giving students the motivation and tools to begin independent research projects as early as possible. Recently, we have further modified the laboratory experience to incorporate sustainability throughout the semester with the aims of exposing students to this critical idea early and often. A particular focus is placed on chemical safety and life-cycle assessment, encouraging students to not only pay attention to the chemicals they are using, but also to think about safer alternatives for both conducting the experiment and ultimately disposing of waste chemicals once the experiment is completed. We encourage students to think about the long-term impacts of the waste they generate and the nuances in all the chemistry they do.

CHED 385

Linking directed essays about current social and political issues to a college-wide citizenship core competency

Mitchell J. Robertson, [email protected]. Southwestern Illinois College, Belleville, Illinois, United States

At Southwestern Illinois College, Citizenship is one of three general education core competencies for all degree graduates. The Citizenship core competency has two tracks: civic and social accountability and personal accountability. Civic and social accountability is a topic that has not been directly addressed, if at all, in our general chemistry courses. In fact, many aspects of the Citizenship core competency are not taught in any particular course; rather, they are developed, augmented, and refined through learning and engagement in other topics in a college environment and experience. In my general chemistry courses, students write directed essays about current social and political issues in science. The essays themselves are part of a module on Blackboard that includes readings from popular media and a multiple-choice assessment about the readings. The students then write the directed essays after completing the readings and assessment. As such, the essays allow for assessment of Citizenship in a chemistry course with an evaluation that is directly related to science. The essays contain a wealth of information about the students' knowledge, disposition, and even actions that pertain to the civic and social accountability track of the Citizenship core competency, as well as to several departmental educational goals. The presentation will include an overview of the Citizenship core competency and an explanation of how data from the essays are linked to departmental and college-wide outcomes.

CHED 386

Using the real world in the chemistry classroom

Cynthia Maguire, [email protected], Nasrin MirsalehKohan. Chemistry & Biochemistry, Texas Woman's University, Denton, Texas, United States

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For almost the past decade, chemistry faculty at Texas Woman’s University have emphasized the use of real world situations and citizen science opportunities as ways of teaching in our classes, whether for majors or non-majors. We have learned a lot about this approach to education as a result. Every citizen needs to understand chemistry, so we have taken the approach that making chemical knowledge applicable to the real world problems we face is nothing less than essential. This has taken many forms which will be included in the presentation. One example is introducing a lecture topic by discussing a related civic issue, such as the recent public debates over fracking to introduce a lecture on work and energy. Another is making a civic engagement assignment in a course so that students must utilize their new knowledge in the community (a high-impact practice). And through our university-wide experiential education program, “Learn by Doing,” we are even partnering with informal science organizations to meet student the student learning outcome, Effectively connect classroom theories to real-world experiences through practical application of knowledge. This presentation will give an overview of the many ideas used, what worked well and what didn’t, and perhaps even what we think we know about why some ideas didn’t work out. We will also preview our newest idea for putting citizen science projects to work in our courses for both chemistry majors and non-majors.

CHED 387

Letters-to-the-editor in an on-line chemistry course

Alton J. Banks, [email protected]. North Carolina State Univ, Raleigh, North Carolina, United States

Chemistry and Society (CH100) is a course designed for non-science-major students at North Carolina State University. The online version of this course featured the construction of "responses" by members of the class to appropriate persons in the form of letters-to-the-editor of a local newspaper, to a congressman, or to the head of a professional organization. The course is organized around the A.C.S Text, Chemistry in Context, and features discussions on topics affecting everyday citizens.

CHED 388

Make your own orange juice and other experiments and activities for consumer chemistry

David A. Katz, dakatz[email protected]. Eductaor/Consultant , Tucson, Arizona, United States

A non-major chemistry course, often a watered-down version of general chemistry, may be the only chemistry course many individuals ever experience. Such a course should discuss a range of topics including consumer products, current issues, and modern technologies rather than reiterating the classic chemical principles in simplified form.

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Also, the general chemistry course should include these topics and issues. This author has modified both the non-major course and general chemistry courses to include a wider range of topics. In addition, this author has presented papers, demonstrations, and hands-on workshops to diverse audiences from pre-K through college students and the general public in schools, museums, hotels, firehouses, and community centers, both indoors and out, to produce informed citizens who can make intelligent decisions on science affecting their lives, society, and related local and national legislative issues.

CHED 389

How much arsenic do we eat? A general chemistry course for non-science majors

Julian F. Tyson, [email protected]. Chemistry Department, University of Massachusetts, Amherst, Massachusetts, United States

I have taught a course with this title in face-to-face (F2F) mode four times and in the online (OL) mode 10 times. About 90% of the material is common to both. Currently (spring 2016), there are 180 students in the F2F version and 17 in the OL version. The course is pitched to students as follows: “How much arsenic do we eat? We'll examine how to answer the question and why we should be interested. Along the way you'll pick up (a) an understanding of how chemical principles can be used to find out about the composition of materials and of the scope and limitations of chemical measurement technology, (b) the background knowledge needed to make a sensible decision about how much rice you should eat, (c) some basic chemistry concepts, and (d) a feel for what it means to think like a chemist." The arsenic contamination of food (principally rice) and drink (principally drinking water and fruit juices) is a topic of current media interest and is thus a real-world problem that affects everyone, as almost everybody, including the students in my classes, eats rice. UMass Amherst expects a 4-credit course to involve 12 hours of relevant study (including class contact) per week. Students write arsenic-related papers on topics selected from a list (of >50) that I have created, write reports on material retrieved from the Web of Science (I create the search parameters), and work on OWL homework (selected assignments from the gen. chem. for scientists course). In the on-line course, there is a series of numerical problem sets on the concept of concentration, which is one of the hardest concepts for many students. Students read a series of papers of increasing technical complexity (starting with Consumer Reports and finishing with PNAS), whose content is examined in the weekly quizzes and the midterm and final exams. In class, as well as some fundamental chemistry topics, I talk about the need for reliable information about chemical composition and explain how difficult this is to obtain for the various arsenic species (some of which are nontoxic) found in food and drink. I explain risk assessment, dose-response relationships, and statistical significance testing, in addition to the basic framework within which science is done. I bring in examples from my own research, one aspect of which is a collaboration with the Museum of Science, Boston to create a citizen-science project that will involve measurements (of the arsenic content of rice) in participants’ own kitchens.

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CHED 390

Whodunit mystery: Using a forensics context in general chemistry

Bradley D. Fahlman, [email protected]. Department of Chemistry & Biochemistry, Central Michigan University, Mount Pleasant, Michigan, United States

Forensics-based television programs remain one of the most popular genres, with many textbooks and teaching materials now featuring forensics-based examples to enhance student motivation and interest. In the spirit of a context-first approach, we will describe the use of a forensics case study for a non-science majors chemistry course, written as a storyline with embedded chemistry content. This context presents an interesting strategy to incorporate a number of fundamental chemistry concepts such as stoichiometry, limiting reagents, reaction classifications, solutions, molarity, and many others.

CHED 391

Involving students in chemistry through real-life connections

Connie Gabel, [email protected]. Chemistry, Metropolitan State University of Denver, Louisville, Colorado, United States

Showing students the relevance of chemistry and how it connects to their lives as well as its relationship to important events in history facilitates interest in a challenging subject. Significant connections can also be made to public health issues to highlight the role of chemistry in solving these dilemmas in a global environment. Current events such as the use of caffeine, its increased availability, and its link to nutrition and health heighten student interest. Creating an awareness of the many chemical compounds present in a substance such as chocolate helps non-chemistry majors realize the complexities of chemistry. Linking the teaching of chemical structures to substances such as ethanol and vinegar connects their understanding of chemistry to everyday life. Discussing the use of the salt form of amine-containing drugs facilitates the understanding of the importance of solubility. Numerous other examples are used to engage students in learning chemical concepts in context.

CHED 392

Team-teaching in first year seminar courses geared toward STEM majors

Karen J. Castle, [email protected]. Chemistry, Bucknell University, Lewisburg, Pennsylvania, United States

This talk will focus on team-teaching in first year foundation seminar courses taught within the Discovery Residential College at Bucknell University. Discovery is a living-learning community for students with a broad interest in science, designed in the fall of

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2013 to encourage high levels of student academic engagement. Students enrolled in Discovery live together, take one of four available first-year seminar courses related to the theme of scientific discovery, experience a variety of co-curricular programming, and work very closely with faculty and student staff members during their first academic year. There are four faculty members associated with Discovery, each teaching one of the four first-year seminar courses and advising 25% of the students. The four seminars meet together weekly for a two-hour block of time known as "common hour" in addition to regular class hours. Team-teaching is used in a variety of ways in Discovery college including the design and implementation of common hour activities, programming for field trips, and oversight of final projects that involve student-made videos. The effectiveness of these team-teaching approaches on success and retention of students in STEM majors will be discussed.

CHED 393

Professor swap: A strategy to promote interdisciplinary learning

Sarah L. Carberry, [email protected]. Chemistry, Ramapo College of NJ, Saddle Brook, New Jersey, United States

One of the four pillars of education valued at Ramapo College, New Jersey’s public liberal arts college is “interdisciplinary” learning. The Professor Swap program teams up faculty and allows them to teach for a day in a discipline outside of their school. During the swap the professors teach for one class period in a different course subject but relate it to their own field of expertise. This pushes intellectual boundaries of both the faculty members and the students. The swap of an Organic Chemistry class (in the School of Theoretical and Applied Science) with Energy and Society class (in the School of Social Science and Human Studies) will be discussed.

CHED 394

Team teaching across the disciplines: An interdisciplinary study of chemistry, religion and philosophy for the development of human meaning and purpose

Karen S. Wendling, [email protected], Patrick McCauley. Chestnut Hill College, Philadelphia, Pennsylvania, United States

In today’s society no one can legitimately afford to ignore chemistry – the information it provides about the past, its modern significance, and its ability to shape the future. Chemistry, like all science, is dedicated to discovery and practical application. As a scientific discipline it is inherently incapable of formulating the ethical boundaries and restriction of its own inquiries. Human beings themselves must bring ethical limits to unbounded scientific curiosity. For many people the introduction of the scientific method actually undermined the credibility of traditional ethical structures which had historically been used to guide scientific inquiry. Questioning traditional ethical structures, often presented as part of religion, can result in a deep uncertainty of one’s own character. A

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team-teaching approach allows for the simultaneous study of chemistry and religion/philosophy which mimics the conflict and ultimate synthesis that must take place in the minds of students as they develop as ethical decision-makers in an age of science. This paper describes two undergraduate courses created and team-taught by the authors, where each author represents a different discipline. The authors have taught two courses exploring the conflict and synthesis between science and religion/philosophy: a discussion-based honors seminar and a summer undergraduate course open to any interested student which fulfills a general education requirement. Both team-taught courses required the students to learn about selected topics in chemistry and religion/philosophy. Specifically students learned about the chemical basis of Darwinian evolution and modern advances in atomic and quantum chemistry. These areas of focus were selected because they represent dramatic shifts in the understanding of humanity’s place in the universe. Students were exposed to the philosophical works of Plato, Kant, Nietzsche, and Schleiermacher while studying these worldview-altering scientific advances. Students were ultimately challenged to develop a new interpretation of the interaction between science and religion by analyzing selections from literature. In addition to describing these courses, this paper details the facilitation process for our discussion-based honors course and the team-teaching approach we applied to the more traditional course that also allowed for chemistry laboratory experiments to be performed by the students.

CHED 395

How to efficiently steer the ship while steering clear of dictatorship

Monica Ilies, [email protected], Daniel B. King. Chemistry, Drexel University, Philadelphia, Pennsylvania, United States

Uniform content coverage, equal student workload, standard benchmark assessments and consistency in grading are significant challenges in large enrollment courses with multiple lecture sections. Working in a team with more than 3 instructors also poses major issues when it comes to ensuring: i) constant high quality of content delivery; ii) fair ethics; iii) common meeting times for accurate planning, discussion of student progress or troubleshooting; and iv) cohesive bridging of diverse expertise, teaching philosophies and personalities without killing creative personal input through rigid rules imposed by a common core. We will present a team-teaching model that we implemented a couple of years ago in a high enrollment course at Drexel University: the introductory general chemistry sequence (CHEM 101-CHEM 102) for STEM majors. Despite the very large scale (~1200 students; 25-30 instructors; 5-6 lecturers; ~45 recitation and ~55 laboratory sections), the model has been successful in solving the above issues, while also providing a nice balance between following instructions and making independent decisions. We use a specific design for the course website, with detailed information, including an exact course schedule that attempts to sync lecture content with recitation, laboratory, and online homework components, while allowing instructors to experiment with different teaching methods and motivational techniques.

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All lecturers participate in the writing of exams. The organization improves from quarter to quarter based on teachers' and students' suggestions. The model is an example of a consistent, yet flexible, collaborative approach that can be easily tailored to any class size and subject matter. We will discuss in detail the logistics and the outcomes, including quantified performance and feedback from both students and instructors.

CHED 396

Six sections, and one syllabus: Team teaching general chemistry

Stephanie M. Taylor, [email protected]. Science and Mathematics Education, University of Texas at Dallas, Richardson, Texas, United States

Team teaching any course comes with rewards and pitfalls. In order to teach over 1,000 general chemistry at the University of Texas at Dallas, a team of 5 instructors gather weekly to ensure we are, in fact, a team. Balancing the ideas of five Ph.D chemists takes a dose of cooperativity, tact and bull-headedness. Yet from potential frustrations comes a course where both students and instructors continue to strive to learn -- even in general chemistry. In our course, a common syllabus helps set the tone for the semester. Common exams written by the current team keep all accountable, while weekly meetings keep each of us on track. Here, the syllabus is set, but the class time is your own. Explore the sections of General Chemistry at a university where exploring and growing into your own teaching philosophy is strongly encouraged, yet we remain coupled to common exams. While frustrating at times, the students clearly benefit from instructors who are on the same page -- often literally.

CHED 397

Team-teaching general chemistry laboratory

Joseph C. Ulichny, [email protected], Sarah J. Hansen, DONGHONG SUN. Columbia Univ Chemistry Dept, New York, New York, United States

This talk will discuss a team-teaching approach for a one semester stand-alone General Chemistry Laboratory course. This course is co-taught by two full time instructional faculty members and encompasses topics from the entire General Chemistry Lecture series in our department. Team teaching this course has proven beneficial for students, as well as the faculty, given the increased flexibility that arises from having two instructors. Additionally, students have the opportunity to get different viewpoints on the same chemistry content, providing opportunities for greater understanding. We will discuss the benefits this teaching approach has on course material development, teaching assistant training, assessments, and administrative aspects. While this collaborative approach has increased consistency in many areas, it has also allowed each instructor freedom regarding lecture delivery.

CHED 398

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Forensic chemistry: a team-taught course with emphasis on student centered learning

Donald E. Mencer, [email protected], Terese Wignot. Chemistry, Wilkes University, Wilkes Barre, Pennsylvania, United States

Forensic chemistry courses are multi-disciplinary by virtue of the subject material. A strong emphasis on analytical chemistry is a must with special emphasis placed on the demands of sampling as it pertains to science that must stand up to scrutiny in the courtroom. Biochemistry underlies forensic examinations related to hairs, bodily fluids (ex. serology), drugs, forensic toxicology, and other areas. Some of the course must also be devoted to an examination of how the science interfaces with the legal system (topics related to criminology and criminal justice). At Wilkes University, a team-approach to teaching a forensic chemistry course (primarily for chemistry and biochemistry majors) has been employed in every offering of the course. The analytical chemist and biochemist involved have utilized a number of strategies to enhance the course. A guest speaker from a local crime lab has been utilized to provide a grounding of the course in the real world. The instructors have also relied heavily on case studies to support the presentation of the scientific foundations for the course. Standard lecture has been augmented with a variety of student-centered approaches to learning. Students have also been expected to develop and implement hands-on projects that have covered areas such as: (a) DNA analysis, (b) fingerprinting, (c) gun-shot residue detection, (d) hair and fiber analysis (by microscopy and spectroscopy, (e) drug detection with both screening tests and follow-up testing (ex. GC-MS detection of cocaine), (f) blood spatter detection, and more. Students also write papers and do classroom presentations on case studies to highlight important applications of science to real-world courtroom cases. Successes and challenges of running a course in this format will be detailed.

CHED 399

Strategies for effective use of thermal laboratory in the courses of thermodynamics, material balance, heat transfer and cleaner production

Gabriel Camargo1, Gonzalo Martinez2, [email protected], Ruth Alejandra Catacoli3, Salvador Vargas2, Robinson Cardona 2, Andrea Ochoa3, [email protected], Carolina Villanueva2. (1) Mechanical Engineering, Universidad Libre, Bogota, Colombia (3) Environmental Engineering, Universidad Libre, Bogota, Colombia

The science students need integrated knowledge to solve the challenging problems in the near future. The thermal plants laboratory can be used as a powerful tool in courses such as Chemistry, material balance, thermodynamic, fluid mechanic, heat transfer and cleaner production among other. These courses are fundamentals in the chemical, environmental, industrial and mechanical engineering programs. Despite of this fact, sometimes the different practices in the laboratory, are routine and boring activities only

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registering data without any challenge labor and without connection between past courses. There are not connection between theory and practice.For example, the unit systems is the first theme in all material balance, thermodynamics and fluids mechanic courses, but is hard topics although was seen in chemistry or physics lectures. Other concept like difference between energy, work and heat are not clear for most students. In thermodynamic the link between the pure substance properties and the tables of them is a very difficult theme, confusing and frustrating. The application of the first law of thermodynamics in control volumes and the table of properties is not a straight linkage. There is more, sometimes the function of equipment is not clear or totally ignored. So the energy balance for specific process equipment has no meaning in the reality. In the heat transfer course, the correlations for heat transfer coefficients are messy and difficult part, Find the appropriate correlation for one process with the right values of the properties of the substances is only part of a routine without real value. . . For all these reason the Mechanical department with the collaborating of Environmental Department, planned a different guide of laboratory linked material balance, fluid mechanics, thermodynamic and heat transfer courses. The plant distribution in the laboratory is used for prepare PFD diagrams and tables, the measure instruments are employed for conversions factors and to calculate Reynolds, and other dimensionless numbers using the thermodynamic properties tables. There are, for now these practices: - Identification system - First law for transient systems - Calculate the correlation for heat transfer coefficient in different heat exchangers - Evaluate the products of combustion. All these activities are thinking for reinforce in the students the concept of the energy, primary energy carrier and the activities related with the cleaner production.

CHED 400

Successfully predicting the product(s) of an inorganic reaction: What are the cues that make this possible?

George M. Bodner, [email protected]. Department of Chemistry, Purdue University, W Lafayette, Indiana, United States

One of the goals of research on problem solving in chemistry is to help teachers better understand how students think in order to develop better instructional strategies to help them learn chemistry. Roughly 50 years ago, in spite of the first author’s strong interest in inorganic chemistry, there was no way for him to predict the product(s) of an inorganic reaction. He either “knew” them because he had seen the reaction (or an analogous reaction) previously or he would have to approach the reaction as something that needed to be “learned.” This paper will compare and contrast the results of a study

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of the performance of individuals from four sample populations on tasks that asked them to predict the product(s) of 20 “simple” inorganic reactions. The sample population (n = 28) included students enrolled in a general chemistry class for engineers; sophomore or junior chemistry majors; graduate students; and faculty who thought of themselves as “inorganic chemists.” Results of this study will be viewed in terms of the meaning of “success” on these tasks, the cues that helped individuals be “successful”, and possible implications this research might have for increasing beginning students’ success on these tasks.

CHED 401

Physical inorganic: Current practices and course impact

Abigail H. Shelton, [email protected]. Department of Chemistry and Physics, University of TN at Martin, Martin, Tennessee, United States

The only inorganic course offered at the University of TN at Martin is a senior level lecture course titled Physical Inorganic. The three-credit hour course is taught every fall and introduces point groups, reducible representations, character tables, molecular orbital theory, crystal field, and solid state chemistry, with an emphasis on connections to physical chemistry. There is an undercurrent of literature throughout the course, culminating in student oral presentations. There is not a laboratory component of the course despite the desire. I will present the course design and expectations, as well as course impact from the perspective of student evaluations and departmental exit exam scores during the four consecutive years I have taught the course.

CHED 402

Humanizing chemistry: Incorporation of cultural themes into the foundational inorganic chemistry sequence

Craig A. Bayse, [email protected], Marie M. Melzer. Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia, United States

The Chemistry and Biochemistry Department at Old Dominion University established a foundational inorganic chemistry course sequence in 2010 in response to revisions to the ACS curriculum. This sequence includes separate lecture and lab courses that require only completion of general chemistry. Students enrolled in this course are traditional chemistry majors from the freshman to senior levels in addition to a larger percentage of chemistry minors from biology and other majors. Due to the wide variety in experiences and backgrounds, the lecture portion was redesigned in recent years to put a human face upon the chemical concepts. Each of the four units concludes with a discussion of a couple of passages from from Hugh Aldersey-Williams' book Periodic Tales relevant to the theme of the unit to supplement the main textbook (Rayner-Canham and Overton's Descriptive Inorganic Chemistry). These discussions bring in the cultural and historical impacts of elements as a means of guiding students toward the

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ubiquitous nature of chemistry in human existence so that they see applications of chemical concepts beyond the course material. To further reinforce this theme, each unit includes discussion board assignments that ask students to look around them to find examples from their life that connect to the course material. The laboratory course was also designed to account for the broad range of experience by front-loading experiments that develop qualitative skills and instrumental tools (IR, UV/Vis, magnetic suspectibility). Labs were selected to engage students' interest through colorful reactions and selected connections to bioinorganic and materials applications.

CHED 403

Cafeteria-style advanced inorganic chemistry curriculum at Luther College

Claude L. Mertzenich, [email protected], Bradley M. Chamberlain. Luther College, Decorah, Iowa, United States

Advanced inorganic chemistry (AIC) teaching at Luther College has undergone significant changes since the introduction of a new cafeteria-style chemistry curriculum ten years ago. Before the 2005-2006 academic year, AIC theory was taught as a traditional semester-long course, without lab, every other year, and it utilized a standard AIC text such as Shriver or Miessler & Tarr. Starting in 2005-2006, AIC coursework was split into three, half-semester courses: (1) Coordination & organometallic; (2) physical inorganic; and (3) solid-state. Although an AIC laboratory had been offered prior to 2005-2006, for logistical reasons it was not highly populated. After 2005-2006, three administrative changes were made to the laboratory course: (1) The lab was moved to the January term; (2) the laboratory became a more significant way for students to satisfy the inorganic portion of the chemistry major; and (3) the lab was also designated as a course which satisfies a certain all-college requirement. Given these laboratory changes, the number of students increased to a sustainable level. The division of the AIC curriculum, as described above, has allowed faculty to teach subjects that correspond better to their areas of expertise and has allowed for more focus and cohesion within the courses. However, some areas of AIC are no longer taught, including acids/bases, redox, and non-aqueous media. The pros and cons of the current Luther College AIC curriculum will be discussed and compared to the former (pre-2006) traditional format.

CHED 404

What about the rest of the elements? How inorganic chemistry fits into a liberal arts education

Jason K. Vohs, [email protected]. Department of Chemistry, Saint Vincent College, Latrobe, Pennsylvania, United States

Most instructors of inorganic chemistry must be selective about what gets included in their portion of the chemistry curriculum. While metals compose the majority of the

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periodic table, are participants in a vast array of chemical applications from catalysis to materials, and produce compounds that have colors that span the visible spectrum, they are often relegated to a tiny fraction of the chemistry program at most colleges. In many cases, a chemistry major may only be required to take a single semester of inorganic lecture, and may be lucky if a lab course has a majority of experiments where carbon is nowhere to be found. Moreover, inorganic laboratory techniques tend to be more involved when air and moisture sensitive reagents come into play. It is imperative that students receive instruction in these techniques to be both competive and safe when they enter the world as professional chemists. How does one choose experiments that both excite and instruct students from among hundreds of potential activities? Herein is described how Saint Vincent College structures its inorganic lecture and lab courses while being attentive to our liberal arts mission.

CHED 405

In or out? Inorganic chemistry curriculum at Barry University

Tamara D. Hamilton, [email protected]. Physical Sciences, Barry University, Aventura, Florida, United States

Inorganic Chemistry at Barry University is a one-semester junior-level course with lab required for all chemistry majors, including those in the biochemistry track. The course roughly follows the content of the first half of Meissler and Tarr's text, with much consideration given to the relevancy of each subject matter to medicine and health care occupations, as roughly two-thirds of students taking the class aspire to those fields. Current coverage includes atomic structure, simple bonding theories, coordination chemistry, symmetry, molecular orbitals and the solid state. The laboratory includes IR and UV-Vis spectroscopy, magnetic susceptibility and working with X-ray crystallography data. Decisions about course content for this and an upcoming elective advanced course will be discussed, as well as how active learning techniques, a literature presentation, and assignments from the Cambridge Structural Database are applied in the course.

CHED 406

Teaching molecular orbital theory in the context of computational chemistry

Ronald See, [email protected]. Chemistry, Indiana Univ. of PA, Indiana, Pennsylvania, United States

Computational techniques are an important and growing part of modern chemistry, and packages to carry out these techniques are easily available and often included in many undergraduate chemistry courses. However, there is often difficulty in translating the computational results into a vocabulary that is recognizable to non-computational chemists. In part, this stems from the way that molecular orbital (MO) theory is presented in inorganic (and other) undergraduate chemistry courses. A survey of

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inorganic chemistry textbooks reveals that MO theory is frequently presented in an abstract context, often containing concepts that inappropriately blend MO and valence bond theory. In contrast, MO theory has been taught at Indiana University of Pennsylvania using an approach that integrates the concepts of MO theory with the computational output of programs such as Gaussian and Spartan. It is believed that this approach makes MO theory more understandable and concrete to the student, and also better equips the student to make use of computational techniques in subsequent research experiences. Examples of this approach, which were used in undergraduate chemistry courses, will be presented.

CHED 407

Incorporation of benchtop NMR spectroscopy into undergraduate inorganic laboratories: An active-learning approach

Susanne Riegel, [email protected], Juan Araneda. Application Chemistry, Nanalysis, Calgary, Alberta, Canada

NMR Spectroscopy is one of the most widely used characterization techniques in chemistry. Despite pedagogical shifts towards active-learning and guided-inquiry approaches, incorporation of NMR spectrometers directly into undergraduate curriculum has remained largely limited due to mitigating factors of size, cost and availability of high-field spectrometers. As a result, students rarely gain hands-on access to this instrumentation, particularly in the beginning stages of their programs. Moreover, as NMR Spectroscopy is primarily introduced in organic chemistry, the majority of undergraduate exposure is strictly in a structural elucidation 1H/13C NMR context. An emergence of a new class of benchtop NMR spectrometers that are affordable and do not require weekly upkeep or maintenance can facilitate the introduction of this technique into beginning or advanced inorganic chemistry courses. Herein, we describe methods for unique incorporation of the NMReady benchtop spectrometer into inorganic undergraduate laboratory experiments, illustrating how students can learn the proper technique to prepare samples, and use other important NMR nuclei (e.g., 19F, 31P) to monitor and characterize reaction mixtures and products.

CHED 408

Developing chemical safety information quality assessment tools

Ralph Stuart1, [email protected], Robert E. Belford2. (1) Dept of Env Hlth Safety, Keene State College, Keene, New Hampshire, United States (2) Univ of Arkansas at Little Rck, Little Rock, Arkansas, United States

Many social issues about chemicals in the environment revolve around chemical health and safety information and its quality. An important emerging resource in this respect is Wikipedia; Wikipedia is one of the top ten most accessed web sites on the Internet and

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the only one that establishes editorial oversight to maintain information quality from anonymous contributors. Entries about chemicals in Wikipedia consist of a structured "Chembox" and the less structured text of the entry. However, for the casual user, it is not clear what the source of the information presented is or its reliability. Thus, the quality of Wikipedia as a general source of this information is unclear. Our work has begun to assess the importance of this issue by harvesting chemical safety information from the Wikipedia Chemboxes and comparing the results to more authoritative sources collected in the PubChem database. This presentation will discuss the variety of uses of chemical health and safety information by the public and what our findings about Wikipedia's information quality suggest about this source of such information.

CHED 409

Assessing the effectiveness of using climate change activities to teach general chemistry content

Daniel B. King1, danie[email protected], Jennifer E. Lewis8, Karen Anderson6, Douglas E. Latch7, Susan Sutheimer5, Gail H. Webster3, Catherine H. Middlecamp4, Richard S. Moog2. (1) Drexel Univ, Philadelphia, Pennsylvania, United States (2) Chem Dept, Franklin Marshall Coll, Lancaster, Pennsylvania, United States (3) Guilford College, Greensboro, North Carolina, United States (4) Nelson Inst for Environmental Studies, Univ of Wisconsin-Madison, Madison, Wisconsin, United States (5) Green Mountain College, Poultney, Vermont, United States (6) Madison College, Madison, Wisconsin, United States (7) Seattle University, Seattle, Washington, United States (8) Department of Chemistry, University of South Florida, Temple Terrace, Florida, United States

Much of the instruction in general chemistry is disconnected from everyday applications. While there are many valid reasons for leaving out these applications (e.g., large content requirements, limited time), this omission likely contributes to the difficulty many students experience in the introductory chemistry courses. One way to address this issue is to use everyday applications as a way to teach general chemistry content, instead of simply including the applications as supplementary examples. As part of an NSF-funded project, we have created a set of in-class activities that use climate change context to teach general chemistry topics. These activities were written using the POGIL (Process Oriented Guided Inquiry Learning) methodology and cover topics from both the first and second terms of general chemistry. In addition to using climate change as a model, each activity includes a section where students use socio-economic data to answer application questions related to the chemistry content. The goal of this part of the activity is to require students to use data in situations where they might previously have simply answered on an emotional level. In an attempt to determine the effectiveness of these activities, we have created two-question assessments associated with each activity. Each assessment consists of one

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question that is focused on the chemistry content and one question that is focused on the climate change context. These assessments were administered during the next class after the activity had been completed. Student scores on these assessments suggest that students are able to demonstrate understanding of both the chemistry content and the climate change context. Key features of one of the activities and the corresponding assessment will be presented.

CHED 410

Helping students place chemistry in its social context through laboratory exercises

Leonard Demoranville, [email protected], Kari Young, Olivia Kane. Chemistry, Centre College, Danville, Kentucky, United States

Centre College’s general education curriculum is formed around several commitments, one of which is “placing the academic discipline and methodologies in context with issues of societal and personal choices”. Prior assessment of our one semester accelerated general chemistry course suggested more emphasis could be placed on helping students form the connection between chemistry and societal issues. Due to the heavy content load of the course, it was determined that re-designing laboratory exercises to achieve content, laboratory skill and social context learning goals would be a possible way to aid students in achieving these connections while maintaining the pace of the course. In the summer of 2015, we revised the laboratory schedule so each lab exercise was formed around a socially relevant question. Most laboratory exercises were modified from existing laboratory manuals and published scholarly literature. The laboratory schedule was implemented in fall of 2015. Student survey data from fall of 2015 suggests that students completing this set of exercises were more aware of the impact of chemistry on societal issues than those that did not. Further refinements to the individual lab experiences are expected to further enhance this connection to social context.

CHED 411

Exploring the triple bottom line through the drug portfolio project

Karen Anderson, [email protected]. Madison College, Madison, Wisconsin, United States

Veterinary technician students take chemistry as part of their 2-year associate degree program. The drug portfolio, a semester-long project, prompts them to apply their chemistry knowledge. Students choose drugs relevant to their program pharmacology course. Throughout the semester, they investigate the various chemical and physical properties of their drugs, such as structure, solubility, and stereochemistry. In addition, this year’s project includes a section on people, profit, and the planet as linked to their

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chosen drugs. See how the students weave sustainability into their projects and what they, as real-world citizens, consider important.

CHED 412

Distributed drug discovery (D3) update: First global student collaboration in neglected disease discovery

William L. Scott3, [email protected], Jack G. Samaritoni3, Lukasz Popiolek5, Amy B. Dounay2, Doug M. Schirch1, Daniel Garcia Rivera4, Anna Biernasiuk6, Anna Malm6, Martin J. O'Donnell3. (1) Chemistry, Goshen College, Goshen, Indiana, United States (2) Chemistry and Biochemistry, Colorado College, Colorado Springs, Colorado, United States (3) Chemistry and Chemical Biology, IUPUI, Indianapolis, Indiana, United States (4) Faculty of Chemistry, University of Havana, La Habana, Cuba (5) Organic Chemistry, Medical University of Lublin, Lublin, Poland (6) Pharmaceutical Microbiology, Medical University of Lublin, Lublin, Poland

The Distributed Drug Discovery (D3) program educates student scientists in applied synthesis and biological evaluation while connecting them with critical humanitarian drug discovery needs. As they learn theory and practice they become part of a large, internationally distributed research resource for the discovery of drugs to treat neglected diseases. We present here our first international collaboration to educate students in the fundamentals of organic synthesis and drug discovery while they search for antibiotic drug leads. It teams students at the Medical University of Lublin (Poland) and three sites in the United States: Colorado College, Goshen College and Indiana University Purdue University Indianapolis (IUPUI). We will partner with the University of Havana in the fall of 2016. Students utilize our simple, inexpensive and powerful D3 Lab 2 procedure (Figure 1) to synthesize, many new molecules for testing as potential antimicrobial agents. This is done in replicated fashion across sites using inexpensive Bill-Board equipment. The molecules made are then sent to Poland for biological evaluation and the results shared with all the participating institutions. Students are given the biological results so that in subsequent syntheses they can use this data to choose, from a limited number of options, the next set of molecules to make. This project trains students in the basic elements of drug discovery, teaches them important synthetic methodology and laboratory procedures, connects them to a critical real-world context – the discovery of drugs for neglected diseases – and brings them into collaboration with international students.

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CHED 413

Civic engagement and undergraduate research:of the student, by the student and for the student

Richard D. Sheardy, [email protected]. Department of Chemistry and Biochemistry, Texas Womans University, Denton, Texas, United States

We now know that a “learn by doing” approach can enhance student learning. We have also discussed and analyzed the role of civic engagement in enhancing student learning in the lecture hall. However, the role of undergraduate research, a perfect example of learn by doing, has not been included in those conversations. As we continue to focus more on improving enduring understanding for students, the incorporation of civic engagement in undergraduate research becomes an apparent approach to that end. The question then becomes “How do we do this without losing content?” The primary avenue to the answer is through the laboratory experience, whether a teaching or a research laboratory. This talk will present strategies for implementation of civic engagement into undergraduate research and will feature examples by faculty who have had success in coupling civic engagement and undergraduate research in both small and large classes at all levels.

CHED 414

What’s in your water? A class tackles PFOA pollution in Bennington, Vermont

Janet B. Foley, [email protected]. Bennington College, Bennington, Vermont, United States

Recently perfluorooctanoic acid (PFOA), a surfactant used in a variety of polymer applications, was discovered in the town water supply and wells in Hoosick Falls, NY and private wells in Bennington, VT. Measurements have recorded concentrations in ppt (parts per trillion). Community members and state agencies are concerned. The properties of PFOA offer challenges to predicting its solubility, its adsorption in soil and its health concerns. Three members of the faculty at Bennington College received a RAPID Response NSF grant to work with students, community members, and state agencies to figure out the extent of contamination of wells, the possible percolation

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routes through the soil and bedrock, and to look at policies that affect the safety classification of industrial chemicals. Through this process we hope to train students how to form questions about chemicals in the environment, how to critically evaluate data, and how to work with different constituencies to generate the best information that we can with what we know.

Structure of perfluorooctanoic acid (PFOA)

CHED 415

Rubric development for judging scientific thought and creativity in the ACS competition, Chemagination

Barbara Ameer1, [email protected], Randy A. Weintraub2. (1) Medicine, Rutgers - Robt Wood Johnson Medical School, Princeton Jct, New Jersey, United States (2) Science Math & Technology, Rowan College at Burlington County, Pemberton, New Jersey, United States

Chemagination is an ACS competition for high school students and is aligned with the ACS goal of fostering “innovative, relevant and effective chemistry education.” Offered annually since 2002, this local section competition at Princeton University has recently grown in popularity. Annual surveys indicated a desire by students for detailed understanding of the 5 categories of scoring. They are scientific thought, creativity of ideas and generating a future solution to improve lives, clarity of communication, thoroughness and teamwork among the 2 or 3 students per team. In response, a rubric was developed for use by the judges, who are 9 doctoral level scientists from the Princeton and Trenton local sections. Methods: From a Scopus literature search on “science rubrics and education,” articles were evaluated for suitability for criteria that has been used over the past 5 years in our local contest, as an interpretation and refinement of judging criteria used upon initiation of the competition. A strawman rubric was compiled by high school and college level educators. Feedback was then obtained from current and past judges of Chemagination, secondary and graduate school educators involved in Chemagination, and a chemistry graduate student. Outcome: The newly created rubric delivers one composite score, rather than separate scores – one for the ChemMatters feature article with magazine cover design and the other for the poster, as an accurate and effective presentation of the article. Judges found the dual scoring process cumbersome and redundant. The final agreed upon

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rubric expands scoring items from 5 to 12, with weightings ranging from 2 to 5 maximum points each, summing to a score of up to 50. Greater weight is assigned to dimensions fundamental to this unique competition, ie, scientific thought and justification, creativity, and team presentation to judges at the poster session. Conclusion: A competition-specific rubric was devised to aid judges and to enrich the quality of interaction between judges and students, with rubric feedback on individual team performance that can guide them in subsequent competitions. Implementation will make the judging process more streamlined, efficient and defensible while enhancing satisfaction with the learning experience for both judges and students.

CHED 416

Theoretical basis for a new set of solubility rules

Richard H. Langley, [email protected], Cassie A. Davis, Monica Cervantes. Stephen F Austin State Univ, Nacogdoches, Texas, United States

The use of “traditional” solubility rules has fallen into disfavor during the last few years, partly because of the decrease in use of qualitative analysis experiments in undergraduate laboratories and partly because the rules appear to be simple memorization without any theoretical basis. In a previous presentation, a set of three “new” solubility rules were offered. At the time, the main emphasis was on the new rules with a minimal discussion of the underlying theory. In this talk, there will be a more detailed discussion of the theoretical basis of these new rules. The solubility of ionic compounds depends on the charges of the ions, the ionic radii, and degree of covalent bonding present. Suggestions on how to present the material to students in introductory chemistry courses will be included to help in the application of the rules to writing correct net ionic equations and to solubility product constant calculations.

CHED 417

New chemistry: Embracing the human element

Tammy Hawley, [email protected]. UNC Asheville, Asheville, North Carolina, United States

In the twentieth century, chemistry’s linear profit-driven model made profound discoveries — and consequently large amounts of toxic waste and byproducts — which greatly contribute to the modern challenges humanity faces. This oversight provoked the adoption of practices and principles such as green chemistry and green engineering as a way to practice high-level chemical experimentation without acting unsustainably. With the growing integration of green chemistry and engineering in industry and academia, Paul Anastas’ talk Green Chemistry Next highlighted the lingering issue of “preventing getting stuck in a metric driven loop”. We began to seek out why this might happen, realizing the necessity to re-ask “What does it mean to be chemists, members

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of society, and human?" In response to these questions, we took a humanistic approach and began to address key components needed to help students rise to the challenges in the new era of chemistry. New chemistry is intended as a guide to allow society and chemists to prosper and grow sustainably, by acknowledging the human element and finding ways to cooperate with it rather than control it. New chemistry encourages a shift away from shareholder and consumer desires as the primary driving force behind research, instead impressing ethical guidelines that assist chemists in devising their new role in society as environmental and social stewards. These guidelines help them to ultimately embrace green chemistry and engineering principles, and avoid reverting to the linear thinking which caused these problems in the first place. The introduction of curiosity as a core component of new chemistry allows for continual expansion and intellectual stimulation of the individual, leading to growth in fundamental research and subsequent applied research opportunities, and making innovative breakthroughs inevitable. These components are essential for tackling the increasingly complex problems humanity faces, such as those recently noted by George Whitesides at Harvard: public health, mega-cities, climate instability, and dissipative systems.

CHED 418

Best practices in peer learning sessions: Advice from peer leaders and peer mentors

Gabriela A. Szteinberg1, [email protected], Michelle Repice2, Regina Frey1,2. (1) Chemistry, Washington University in St. Louis, Saint Louis, Missouri, United States (2) Teaching Center, Washington University in St. Louis, Saint Louis, Missouri, United States

Peer learning programs in science courses allow for deeper and more effective learning. At Washington University in St. Louis, we provide Peer-Led Team Learning and Chemistry Peer Mentoring programs to enhance student success in the General Chemistry course sequence. New peer leaders and peer mentors are trained through a seminar course on academic mentoring. The final project in this course is a book with essays providing advice, written by each new peer leader and peer mentor. We analyzed twelve years of peer leader and peer mentor advice books using qualitative discourse analysis and a community of practice theoretical lens, to identify which challenges were encountered by the peer leaders and peer mentors during their first semester of leading/mentoring. The peer leaders/mentors also described strategies to deal with the challenges. We present the main challenges faced by peer leaders/mentors and their advice or best practices to deal with the challenges. Instructors may use this advice in their own courses or for training in their peer learning programs.

CHED 419

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Implementation of the semi-flipped classroom model: case studies

Alison Keimowitz, [email protected], Zachary Donhauser, [email protected]. Vassar College, Poughkeepsie, New York, United States

In summer 2015, both authors participated in a workshop training instructors on using technology to flip the classroom and provide context outside of class while allowing more active learning exercises during class time. Both authors used this training to adopt a semi-flipped structure, producing short videos in lieu of in-class lecture on an approximately weekly basis, for courses that had previously been taught without the use of any videos. The courses modified were at the introductory level, general chemistry, and at the advanced level, the thermodynamics semester of physical chemistry. In both general chemistry and physical chemistry the same end-of-term exam was given both before and after the course structure modification. Results of this assessment, student comments, and instructors’ subjective impressions will be presented.

CHED 420

Thinking about problem solving: writing a recipe

James F. Kirby, [email protected]. BC-SCI, Quinnipiac Univ, Hamden, Connecticut, United States

Asking a student “How did you solve that problem?” often leads to shrugs and stares. To make them think about process, a problem was presented and the students were asked to write out a “recipe” for solving the problem: every step that would be followed to complete the problem. After that was complete, students were asked to try to solve the problem, using their recipe and to note any spot where they realized what was missing. Student comments on the exercise will be presented.

CHED 421

Elucidating the formula for enhanced student achievement: Assessment of student performance in general chemistry at a University in Jamaica

Kamilah S. Hylton, [email protected], Natalie Guthrie-Dixon. Chemistry, University of Technology, Jamaica, Kingston, Jamaica

Prior to 2009, Chemistry was taught separately to engineers, chemistry majors and to those in the health sciences such that there were three different Chemistry modules being taught to first year students. A curriculum review, coupled with a financial evaluation led to the conclusion and consequent decision that it would be most efficient to offer a single General Chemistry module to first year students required to take a chemistry module. Since its inception, however, the module has been plagued with underperformance which required that an anomaly report be written for virtually every year. Anecdotally, the blame has been placed solely on the fact that the module is

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pitched at a level that is far above the ability of the students and so it needs to be made simpler and certain content removed. This paper seeks to review student performance over the past six years since its inception with a view to identifying trends and assessing interventions so that more informed decisions can be made to enhance student achievement of learning outcomes in General Chemistry I.

CHED 422

General chemistry performance as a predictor of performance in organic chemistry

Andrew G. Karatjas2, [email protected], Jeffrey A. Webb1, [email protected]. (1) Chemistry , Southern Connecticut State University , New Haven, Connecticut, United States (2) Science Department, Johnson and Wales University, Providence, Rhode Island, United States

A high level of student performance in organic chemistry is dependent on mastery of key topics from general chemistry courses. However, a high grade in a general chemistry course does not always lead to a successful outcome in organic chemistry courses. In this study, we explore this topic. Students in general chemistry I & II take the American Chemical Society final exams. As this exam is used in all of the general chemistry courses at Southern Connecticut State University, it provides a common measuring point for those students. Performance on both final exams was compared to student performance in subsequent organic chemistry courses. In addition to comparing the overall result, questions on the final exams were categorized by subject and performance in specific subject areas were compared to performance in organic chemistry to examine the subjects that show correlation to high levels of performance in organic chemistry.

CHED 423

Flipped learning in the broadcast chemistry class

Michael A. Christiansen, [email protected]. Chemistry & Biochemistry, Utah State University, Vernal, Utah, United States

In flipped classrooms, lecture is pushed outside of class through online videos (content delivery), which frees up in-class time for active, higher-learning activities. Despite a growing literature focus on flipped learning over the past five years, little attention has been paid to flipping classes that are simultaneously broadcast to multiple geographic locations. In such settings, the perceived divide between instructors and distance-site students is greater, adding another variable to the unique dynamic of flipped learning. In this talk, I will discuss three years of experience at flipping broadcast courses, and I will share my strategies for shrinking the perceived divide between the instructor and distance students. This involves a holistic balance of engaging instruction, classroom technology, and online videography.

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CHED 424

Conducting productive online office hours and review sessions from home through desktop streaming programs

Meagan K. Mann, [email protected]. Department of Chemistry, Austin Peay State University, Clarksville, Tennessee, United States

While technology has brought us a great deal of convenience, it has also brought frustration through its limitations. A particular concern for chemistry instructors is the inherent limitations of communicating chemistry via an email system. Students and instructors alike have experienced the frustration of attempting to communicate complex equations and structures through a standard alphanumeric keyboard. One way to circumvent this issue is through the use of desktop streaming services; a sector of online technology that brings a streaming video of your computer desktop to remote users. Presented here is an outline and tutorial of desktop streaming technologies and how they can be utilized to conduct productive online office hours and review sessions for your students.

CHED 425

Using Facebook as a platform for role-playing case studies in the general chemistry course

Andrea Geyer, [email protected]. Chemistry and Mathematics, University of Saint Francis, Fort Wayne, Indiana, United States

This presentation will highlight the design, implementation, and assessment of using Facebook as a tool for role-playing case studies for a general chemistry course. The

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creation of two case studies designed to appeal to broad range of science majors will be detailed. The importance of role playing a broad range of societal members from non-degree personas to scientists to CEOs in order to understand the need for scientific literacy in the public sector will be included. The intentional selection of recent well-known topics in the scientific literature that can generate bias, controversy, and ethical scenarios as central themes in the case studies will be discussed. An analysis of student feedback and learning assessments including database searching, recognizing bias, case study execution, and student reflections will be presented.

CHED 426

Mobile app and web-based audio-visual technology tools to enhance students learning in a general chemistry course

Ganesh Naik, [email protected]. Chemistry, College of Saint Mary, Omaha, Nebraska, United States

General Chemistry course is a prerequisite course for a First Year Science and Engineering majors. The students enrolled in this course have varied level of interest in chemistry. As an educator, we need to utilize different teaching strategies to engage the students in learning and appreciating fundamental concepts in chemistry. This paper discusses the efficient use of web-based audio-visual materials and iOS and Android tablet/mobile phone applications to enhance student learning The mobile applications were used as interactive tools in classroom instruction and to review important chemistry concepts such as atomic structure, periodic table, properties of the elements, chemical bonding etc. In conjunction with these technology tools, online quizzes on the material were developed to assess the student learning outcomes. The intended outcome of this activity was to reinforce the discussion of difficult course concepts and to improve student performance on course examinations. At the end of the semester, assessment data was collected in the form of students’ reflections, course evaluations, and grades. The data collected over the last three years clearly suggests that student confidence in regard to the chemistry concepts increased tremendously as compared to that of previous semesters, and there was a significant reduction in the number of students failing or withdrawing from the first year general chemistry course.

CHED 427

Development of pocket size personal servers for use in the classroom: Hardware and software aspects of them

Joseph Solch1, [email protected], Christina S. Gilpin2, Roger K. Gilpin1, [email protected]. (1) Chemistry, Wright State University, Dayton, Ohio, United States (2) Select-O-Sep, Freeport, Ohio, United States

Online courses fit into two general categories: those that are taught: 1) completely in the distance learning mode, and 2) in the classroom with the Web-material used to enhance

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learning. Likewise, Web-based delivery has gone from its infancy, just two decades ago, to a commonly used teaching tool that has been delivered, almost exclusively, over the Internet using centrally located servers maintained by public and private facilities. In more limited use are the personal servers of some educators that are accessible via the Internet. Unlike the latter case, Part I. of today's two part talk will consider various hardware and software aspects of fabricating miniature servers that will fit in the palm of your hand and can be transported to and used locally in the classroom. The talk is intended to be technical enough for geeks to assemble their own systems but will also provide access to premade images for those with less skills. Two different types of hardware will be discussed that are based on either the use of: 1) Raspberry Pi microcomputers (ARM processors), or 2) “plug and play” microstick computers (Intel ATOM processors). Both systems have wireless and Bluetooth accessibility. Their onboard memory ranges from one to two GB and they have USB support and microchip storage capability. The capabilities and limitations of the hardware will be discussed, as well as development issues related to the use of both Linux and Windows operating systems in terms of the pros and cons of each. The units will be demonstrated onsite for those that bring a portable device with wireless capability.

CHED 428

Development of pocket size personal servers for use in the classroom: Application of these devices to teach quantitative analysis

Roger K. Gilpin2, [email protected], Christina S. Gilpin1, Joseph Solch2. (1) Select-O-Sep, Freeport, Ohio, United States (2) Chemistry, Wright State University, Dayton, Ohio, United States

Online courses fit into two general categories: those that are taught: 1) completely in the distance learning mode, and 2) in the classroom with the Web-material used to enhance learning. Likewise, Web-based delivery has gone from its infancy, just two decades ago, to a commonly used teaching tool that has been delivered, almost exclusively, over the Internet using centrally located servers maintained by public and private facilities. In more limited use are the personal servers of some educators that are accessible via the Internet. Since 2001, the authors have been using this mode of Internet delivery for the instructional materials (i.e., centrally located servers) in freshman chemistry for majors courses, advanced junior and senior analytical courses, and post-B.S. graduate courses. However, unlike delivery, over the fifteen year period that today's talk will consider, significant changes in the way many students interact with Internet-based materials has changed significantly. Initially students used either desktop or laptop computers equipped with word processing, spreadsheet, and presentation software as well as adequate size displays. This was true for a time period from 2001 until about 2010 to 2011. However, with the introduction and proliferation of handheld devices (i.e.,

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smart phones) and social media, many students’ learning expectations and work habits have changed dramatically. Part II of today's two part talk will consider the use of miniature servers that will fit in the palm of your hand and can be transported to and used locally in the classroom as well as allow students to use the device remotely to control chemical instrumentation and process data in the laboratory. The talk is intended to discuss the use of these devices under actual course conditions and to point out their pros related to course management issues.

CHED 429

Teaching large groups of students with online and offline tools: GENI for local authentic research and translation tools for global bilingual lectures

Benjamin J. McFarland, [email protected]. Seattle Pacific Univ, Seattle, Washington, United States

Internet and computer tools have transformed my experiences educating large groups of students in two very different contexts: teaching chemistry lecture/lab courses to dozens of students in the U.S. and teaching pathological biochemistry lecture courses to hundreds of students in Burundi. 1.) In the U.S., one educational problem that technology can address is how to facilitate authentic research experiences in the classroom for large numbers of students. The collaborative online platform GENI (Guiding Education through Novel Investigation) provides an application that transfers protocols among institutions and into undergraduate teaching laboratories, then collects the data from students for analysis and publication. I have used this tool for several years to conduct bioinformatics research with four 16-student lab sections and to prepare recombinant immunoproteins with two 16-student lab sections, and others have used it in molecular biology and genetics contexts. Education researchers on our team developed and applied qualitative and quantitative assessment tools to measure the effectiveness of GENI. The results from these assessments shaped our use of GENI as a tool, and showed that students achieved distinct learning gains from these authentic research experiences. 2.) In Burundi, at Hope Africa University in Bujumbura, I spent a sabbatical teaching pathological biochemistry in English to large groups of Francophone medical students. The variable nature of online access (and electrical power) required different strategies in this context, including off-line or limited-bandwidth solutions for using computers in teaching. These challenges were met with specific hardware and software solutions, which allowed the course to be translated and taught to different groups of students at different times, as assessed by a multiple-choice final exam that more than 200 students passed as part of their medical school curriculum.

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These experiences show how, even with different technological strategies in different contexts, technology can form chemical thinkers in large student groups.

CHED 430

Using technology to flip general chemistry courses in a large public university setting

Melissa A. Deri1, [email protected], Donna McGregor1,2, Pamela Mills1,2. (1) Department of Chemistry, Lehman College of the City University of New York, New York, New York, United States (2) Ph.D. Program in Chemistry, The Graduate Center of the City University of New York, New York, New York, United States

It has been well established that active learning strategies encourage student learning more effectively than traditional lecture-based teaching. However, it can be a struggle to both deliver content and institute active learning practices in the classroom, especially in such a content-heavy discipline like chemistry. One approach to increasing active learning time is to move the content delivery outside of the classroom, most often through online lectures or videos. This shift, known as flipping the classroom, opens up class time and provides the opportunity for more interactive and engaging teaching practices that can reach students with more varied learning styles. An improvement in student performance in a flipped classroom represents the power of active learning as well as the effectiveness of the flipped course design and the new methods of content delivery. In this study, we present student performance data from flipped general chemistry courses run collaboratively at two colleges within a large public university system in an urban setting. The courses were flipped by creating a specialized course website where students could access a series of custom videos with linked online homework. Additionally, since the flipped courses were run with small through very large class sizes ranging from about 20-1000 students, student response devices were incorporated into the course for in-class problem solving sessions. We will discuss the technologies integrated into the course, both in and out of the classroom, as well as the effects of flipping on student performance outcomes.

CHED 431

Chemistry teaching fellowship program at the University of Toronto: Thirteen years of student-driven curriculum renewal

Kris S. Kim2, [email protected], Darius Rackus2, Scott A. Mabury1, Barb Morra2, Andrew Dicks3. (1) Univ Toronto Chemistry Dept, Toronto, Ontario, Canada (2) Chemistry, University of Toronto, Toronto, Ontario, Canada (3) Chemistry, University of Toronto, Ajax, Ontario, Canada

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The Chemistry Teaching Fellowship Program (CTFP) is offered to graduate students and postdoctoral researchers at the University of Toronto as an opportunity to undertake curriculum development and chemistry education research. Program projects are run with faculty supervision and have focused on designing new laboratory sessions, lectures, and tutorials. In its thirteen-year history, many CTFP projects have been implemented in the undergraduate curriculum and some have been published in the Journal of Chemical Education. The history of the CTFP and its impact on undergraduate education and graduate student professional development will be presented, with a selection of projects used as case studies. The CTFP provides a successful model of student-driven curriculum development that can be incorporated in other chemistry departments.

CHED 432

STEM Academy: A bridge program for scholars

Robbie Montgomery, [email protected]. University of Tennessee Martin, Martin, Tennessee, United States

The STEM Academy is a two-week summer program to prepare students to be successful in their STEM courses at The University of Tennessee at Martin. The program is being developed to assist in increasing student preparedness in challenging STEM courses and in turn increase retention rates of STEM majors. Currently students receiving the S-STEM Scholarship at UTM are required to participate in the academy each summer. The program is designed to meet the needs of the scholars and covers courses in chemistry, biology, geosciences, mathematics, computer science and engineering. The course content is tailored to the needs of the scholars to review material that they are weak in and to introduce material they will see in the upcoming semester to ideally give them a head start. This talk will focus on the design and implementation of the program at UTM, as well as the successes and failures of the academy to date.

CHED 433

Developing a peer-educator training curriculum for the SAGE-Chemistry academic support program

Claire J. Siburt1,2, [email protected], Ian Stewart2, Donna M. Hall1. (1) Academic Resource Center, Duke University, Morrisville, North Carolina, United States (2) Chemistry, Duke University, Durham, North Carolina, United States

The Science Advancement through Group Engagement (SAGE) Program is an academic support program for diverse learners that combines facilitated learning communities with individualized learner development and is tied directly to individual chemistry course sections. SAGE was launched in 2009 by the Academic Resource Center in conjunction with curricular reform in the Chemistry Department at Duke

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University. SAGE has successfully supported multiple cohorts of diverse and underrepresented learners in gateway chemistry courses. Data on the effectiveness of the pilot SAGE Program and a description of the Problem Manipulation Methodology now used in SAGE have been published in J. Chem. Ed. Recent funding from an institution-wide HHMI grant, has allowed dedicated staff to expand the reach of SAGE to include an integrated peer-educator development component. Peer-educators are undergraduate students that have succeed in gateway chemistry courses and serve as facilitators of small group learning communities or as one-on-one tutors. Significant restructuring of the training and support of peer-educators has included developing a training curriculum for chemistry peer-educators and operationalizing logistics such as recruiting, payroll, and promotion of peer-educators. The peer-educator training curriculum includes content and skills ranging from management of group dynamics, principles from educational psychology and the learning sciences, innovations in chemical education research and pedagogy, the ethics of mentoring, and diversity topics such as implicit bias and stereotype threat. Evidence of peer-educator development is captured using multiple qualitative measures over time and will be discussed. Feedback from both the students and the peer-educators is collected regularly and will be presented. Supervision methods and associated professional development opportunities for graduate students will also be presented.

CHED 434

Training tomorrow’s chemists in Florida International University, the largest public Hispanic serving institution

Vasileios Anagnostopoulos, [email protected], Leonel Lagos, Ines Triay. Applied Research Center, Florida International University, Miami, Florida, United States

FIU, the largest public Hispanic serving institution in the continental United States (with a project of 65,000 students by 2018), is one of the nation’s largest producers of scientists and engineers from underrepresented groups (over 61% Hispanic and over 13% African American). The Applied Research Center (ARC) at FIU has focused on bringing both undergraduate students and graduate students to the forefront of research and professional training through the DOE-EM workforce development program under a Cooperative Agreement with the US Department of Energy’s Office of Environmental Management. This is an innovative program designed to create a “pipeline” of minority scientists and engineers specifically trained and mentored to enter the DOE workforce in technical areas of need, such as chemistry, cyber security and materials science, in collaboration with academic, government and DOE contractor organizations. Furthermore, the ARC-FIU coordinates the FIU Nuclear Research Program and collaborates closely with the Department of Chemistry in the recently inaugurated Radiochemistry track PhD. This track will prepare students with an interest in the broader chemical aspects of nuclear and radiological sciences, with coursework and research experience at the doctoral level. Graduates of the program will be able to find employment in these areas in industry, government, and academia.

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CHED 435

Increasing biological content in the typical organic chemistry course

Steven A. Fleming, [email protected]. Dept of Chem, Temple Univ, Philadelphia, Pennsylvania, United States

The teaching tool “Bio-Organic Reaction Animations” (BioORA) is a program designed for instructors of organic chemistry, if they choose to cover the supramolecular organic events that occur in bio-organic chemistry. It is also a tool for instruction in biochemistry. The timing for developing BioORA fits perfectly with the new MCAT, which has an emphasis on biochemistry. The timing also has a natural fit with the more visual oriented student learning styles. We will discuss data that suggests students are increasingly turning to online teaching tools in favor of textbooks. The material in BioORA includes: enzymes, lipids, carbohydrates, and nucleic acids. We have 23 animations designed to help students understand and explore the 3D nature of biomolecules. BioORA is available online at no cost to the user. It is compatible with Mac and PC platforms. A review of the content of this software and the results of assessment of BioORA will be presented.

CHED 436

POGIL in organic chemistry lecture: implementation and evolution

Sarah S. Preston, [email protected]. School of Arts & Sciences, Ursuline College, Mentor, Ohio, United States

This presentation will discuss the changes and adjustments made to the format of an organic chemistry lecture course intended for chemistry and biology majors taught at a small, Catholic, women-focused, liberal arts college. Ten years ago, the course was taught in the traditional lecture format and utilized "clickers" and other in-class group problem solving activities. On-line lectures were created, at first as a necessity, for the second semester of the course because of the smaller number of students and the amount of classes missed by students due to snow days, athletic contests, and family obligations. Eventually that entire course was tranformed to a flipped/POGIL format. The first semester organic chemistry course was then converted beginning with the later topics of the course, until finally, the entire year was converted. The last two years have introduced McGraw-Hill's LearnSmart and Connect on-line activities and assessments as pre-lecture preparation and post-lecture review.

CHED 437

Transitioning to a mechanism-based approach in undergraduate organic chemistry lecture

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Anne R. Szklarski, [email protected]. King's College, Wilkes-Barre, Pennsylvania, United States

For many years the organic chemistry curriculum at King’s College, a small liberal arts school in Pennsylvania, has focused on introducing reactions and concepts according to functional group. In an effort to have students develop a deeper understanding of the material rather than rely on rote memorization, the chemistry department recently transitioned to a mechanism-based approach. The effects of this change were examined using student performance on exam questions. These questions, focused on drawing reaction mechanisms, predicting products, and developing synthetic routes, were compared for groups of students before and after the curriculum change. The results of this analysis, along with the benefits and challenges associated with content reorganization, will be discussed.

CHED 438

Increasing STEM retention through multiple programs within chemistry program

Fehmi Damkaci, [email protected]. Department of Chemistry, SUNY Oswego, Oswego, New York, United States

We have developed a peer-mentorship program, introductory math for chemists course, fresman seminar course for majors, as a part of our NSF STEP grant program, to increase the retention STEM. Curriculum for the peer mentorship program weas developed by surveying freshman chemistry students' interest and expectations. The peer mentorship was embeded into general chemistry laboratories, and therefore provided to all STEM students taking general chemistry courses. In its third year, peer mentorship the program attracted great interest from junior and senior chemistry students who would like to be peer-mentors by taking one credit course. Both freshman students and peer-mentors are surveyed at the beginning and the end of the semester. More than 86 % of the students (n=756) who attend one of the sections with peer-mentors taught that it was helpful for them to understand the chemistry concepts in the lab. Students also indicate that peer-mentorship program made them aware about research possibilities on campus, how to reach out to the faculty members, etc. Peer mentorship within introductory labs resolves the problems of scheduling peer mentor/mentee meetings. It allows each student in the lab meets weekly for 3 hours with a mentor, which provides ample time to talk while reactions take place. It is easy to implement at no cost by using current structure in place. It allows setting up the curriculum for the peer-mentorship based on the freshman interest. It is helpful in developing teaching and networking skills in peer-mentors before they graduate. retention rates of the cohorts with and without peermentrhisp will be discussed. In addition, introductory math course for chemist to help student at pre-calculuas level with their chemistry courses was developed. The curriculum of the courses and lessons learned will be discussed. Also, the curriculum and survey results from feshman chemistry seminar course will be discussed.

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