Searching theSearching theChemical Literature: Chemical Literature: Reference Books and Reference Books and

Online ResourcesOnline Resources

Dr. SheppardDr. Sheppard

Chemistry 4401LChemistry 4401L

Why search?Why search?

Physical propertiesPhysical properties– Melting point, boiling point, flash point, Melting point, boiling point, flash point,

refractive index, density, solubility data, refractive index, density, solubility data, toxicity data toxicity data

Developing a synthesisDeveloping a synthesis Experimental proceduresExperimental procedures Spectroscopy dataSpectroscopy data

– FTIR, FTIR, 11H-NMR, H-NMR, 1313C-NMR, MS, UV-VISC-NMR, MS, UV-VIS

Background for researchBackground for research

Where search?Where search?

Reference booksReference books

– Merck IndexMerck Index

– CRC Handbook of Chemistry and PhysicsCRC Handbook of Chemistry and Physics

– March’s March’s Advanced Organic ChemistryAdvanced Organic Chemistry

ArticlesArticles

– Google? Google Scholar?Google? Google Scholar?

– American Chemical Society PublicationsAmerican Chemical Society Publications

The Merck IndexThe Merck Index

A one-volume encyclopedia of chemicals, A one-volume encyclopedia of chemicals, drugs and biological compounds drugs and biological compounds

Contains more than 10,000 monographsContains more than 10,000 monographs– concise descriptions of a single substance or a concise descriptions of a single substance or a

small group of closely related compounds small group of closely related compounds First published in 1889First published in 1889 Now the standard reference for chemists, Now the standard reference for chemists,

biochemists, pharmacologists, biochemists, pharmacologists, pharmacists, and related professionalspharmacists, and related professionals

Compounds in the Merck Compounds in the Merck IndexIndex

Human and veterinary drugs Human and veterinary drugs Biologicals and natural products Biologicals and natural products Plants and herbal medicines Plants and herbal medicines Nutraceuticals and cosmeceuticals Nutraceuticals and cosmeceuticals Agricultural chemicals Agricultural chemicals Industrial chemicals Industrial chemicals Laboratory reagents and catalysts Laboratory reagents and catalysts Dyes, colors and indicators Dyes, colors and indicators Environmentally significant substancesEnvironmentally significant substances

Information in the Merck Information in the Merck IndexIndex

Chemical, common and generic names Chemical, common and generic names Trademarks and associated companies Trademarks and associated companies CAS Registry Number CAS Registry Number Chemical structure Chemical structure Molecular formula and percentage composition Molecular formula and percentage composition Capsule statement identifying compound Capsule statement identifying compound

classes and scientific significanceclasses and scientific significance Scientific and patent literature referencesScientific and patent literature references Physical and toxicity data Physical and toxicity data Therapeutic and commercial uses Therapeutic and commercial uses Caution and hazard information Caution and hazard information

Also in the Merck IndexAlso in the Merck Index

IndicesIndices– Name, Formula, CAS Registry NumberName, Formula, CAS Registry Number

Supplementary tables (some editions)Supplementary tables (some editions)– Physical, chemical and biomedical dataPhysical, chemical and biomedical data– Listings of pharmaceutical company names Listings of pharmaceutical company names

and locationsand locations– Experimental drug codesExperimental drug codes

Organic Name Reactions section (some Organic Name Reactions section (some editions) editions) – Over 450 reactions featuring descriptions, Over 450 reactions featuring descriptions,

literature references and graphical depictionsliterature references and graphical depictions

Merck Index, 14Merck Index, 14thth ed. ed.Entry for cholesterolEntry for cholesterol

Merck Index, 14Merck Index, 14thth ed.ed.Registry IndexRegistry Index

Merck Index, 14Merck Index, 14thth ed.ed.Chemical Formula Chemical Formula IndexIndex

Merck Index, 14Merck Index, 14thth ed. ed.Name IndexName Index

Merck Index, 14Merck Index, 14thth ed. ed.Entry for heroinEntry for heroin

CRC Handbook of Chemistry CRC Handbook of Chemistry and Physicsand Physics

Table of Physical Constants for Table of Physical Constants for Organic CompoundsOrganic Compounds

Listed in alphabetical order by parent Listed in alphabetical order by parent namename– 2-phenylethanol is under ethanol, 2-2-phenylethanol is under ethanol, 2-

phenylphenyl Abbreviations, subscripts, superscriptsAbbreviations, subscripts, superscripts

– Example: what does it mean if a boiling Example: what does it mean if a boiling point is listed as 254point is listed as 254760760, 124, 12434 34 ??

CRC Handbook, 42CRC Handbook, 42ndnd ed. ed.Entry for cholesterolEntry for cholesterol

CRC Handbook,42CRC Handbook,42ndnd ed. ed.Abbreviations for tableAbbreviations for table

CRC Handbook, 42CRC Handbook, 42ndnd ed. ed.Entry for methyl benzoateEntry for methyl benzoate

CRC CRC Handbook, 1Handbook, 1stst

student student editionedition

Entry for Entry for cholesterolcholesterol

Organic ReactionsOrganic Reactions

Organic SynthesisOrganic Synthesis

– 11 collective volumes11 collective volumes

– Search using substructure, reaction, keyword, Search using substructure, reaction, keyword,

name, CAS number, or volumename, CAS number, or volume

March’s March’s Advanced Organic ChemistryAdvanced Organic Chemistry

MarchMarch, 4, 4thth ed.ed.

March, March, 44thth ed. ed.

So, where are the reference So, where are the reference books?books?

CRCCRC– CSU Library (currently being repaired)CSU Library (currently being repaired)– Dr. Sheppard’s office (Student and regular editions)Dr. Sheppard’s office (Student and regular editions)– Chemistry lab (2 editions)Chemistry lab (2 editions)

Merck IndexMerck Index– Dr. Sheppard’s office (1 copy)Dr. Sheppard’s office (1 copy)– CSU Library (1 copy on reserve under General CSU Library (1 copy on reserve under General

Chemistry)Chemistry) March’s March’s Advanced Organic ChemistryAdvanced Organic Chemistry

– Dr. Sheppard’s office (2 editions)Dr. Sheppard’s office (2 editions)– CSU Library (2 in circulating collection, 1 in CSU Library (2 in circulating collection, 1 in

reference collection)reference collection)

Journal Articles and Journal Articles and DatabasesDatabases

Primary (original) vs. Secondary Primary (original) vs. Secondary (reviews, accounts)(reviews, accounts)

Journal abbreviations (see next slide)Journal abbreviations (see next slide)

Journal Articles and Journal Articles and DatabasesDatabases

Chemical Abstracts, BeilsteinChemical Abstracts, Beilstein SciFinderSciFinder Google ScholarGoogle Scholar ACS PublicationsACS Publications

– Available on-campus onlyAvailable on-campus only– Content = 1996 to present

Pre-1996 available through interlibrary loan

– Chemical and Engineering NewsChemical and Engineering News GALILEOGALILEO JStor (JStor (ScienceScience))

Websites Websites

When to use the web instead of When to use the web instead of reference books or journal databases?reference books or journal databases?

Is Wikipedia a good resource?Is Wikipedia a good resource? Use websites with caution!Use websites with caution! Always provide citation with web Always provide citation with web

address and date website was address and date website was accessedaccessed

Don’t forget about textbooks as good Don’t forget about textbooks as good resourcesresources

Spectroscopy websitesSpectroscopy websites

National Institute of Standards and National Institute of Standards and

Technology Chemistry WebBookTechnology Chemistry WebBook

– Mass Spectrometry and Infrared Spectroscopy Mass Spectrometry and Infrared Spectroscopy

data, thermochemical data, and much, much data, thermochemical data, and much, much

more.more.

Spectral Data Base System for Organic Spectral Data Base System for Organic

Compounds (SDBS)Compounds (SDBS)

– Huge searchable database of spectra, including IR, Huge searchable database of spectra, including IR,

NMR, and MS.NMR, and MS.

Safety InformationSafety Information

Vermont SIRI MSDS CollectionVermont SIRI MSDS Collection– Provides access to Material Safety Data Provides access to Material Safety Data

Sheets directly from chemical Sheets directly from chemical manufacturers and from an online manufacturers and from an online database. Chemical Toxicity reports can database. Chemical Toxicity reports can also be found at this site.also be found at this site.

Physical ConstantsPhysical Constants

Fundamental Physical Constants from Fundamental Physical Constants from NISTNIST– Provided by the Fundamental Constants Provided by the Fundamental Constants

Data Center of the National Institute of Data Center of the National Institute of Standards and Technology Physics Standards and Technology Physics LaboratoryLaboratory

ChemDraw Std 14.0ChemDraw Std 14.0

Download the programDownload the program– http://sitelicense.cambridgesoft.com/

sitelicense.cfm?sid=2560– Use Internet Explorer or FirefoxUse Internet Explorer or Firefox– Use your CSU email to log on and follow Use your CSU email to log on and follow

instructions to download the programinstructions to download the program– Earlier versions of the program are Earlier versions of the program are

acceptableacceptable Program tutorialProgram tutorial