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Albert Einstein

CHAPTER – 2

LITERATURE SURVEY

Chapter 2 | Literature Survey

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2.0 Introduction

In connection with the backbone of investigation, many authors have been

studied to gain knowledge in the field of molecular interactions between amide,

amines with alcohols. Because of these two organic groups are more important in

biological organic compounds for existing life.

Researchers all over globe have been studied to understanding mystery of

natural phenomenon involves in the interaction between matter and energy. Also to

known H-bonding interactions involved in the alcohol-amines and alcohol - amide

systems to investigate using different Physico-chemical techniques.

In recent years different reviewers are studied interaction involved in

alcohol with amides and amines systems by using different Physico – chemical

methods. The role of hydrogen bond is very important to understand biological as

well as chemical organic compounds in terms of its constituents. The chemical

compound of liquids involved in interaction can be established by nature and strength

of complex.

An excellent review of literature work provides information regarding

molecular behavior of liquids. This chapter gives insight into different

Physico-chemical method, in-terms number of thermodynamic parameters like

dielectric constant, dielectric relaxation time and viscosity, density etc.,

This chapter is intended to provide information about previous studies related

to dielectric, spectroscopic and ultrasonic studies pertaining to amides and amine

substitutes for binary and ternary organic liquids mixtures are outlined.


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2.1 Dielectric study

This section explains brief earlier studies which gives significant amount

information about the study carried by several workers to determine different

dielectric parameters using different dielectric experiments techniques, their findings

and conclusion.

The dielectric properties of a substance such as dielectric constant, dielectric

loss, relaxation time provide an insight into structure of molecules in the

system. In liquids, molecule has rotational freedom and its dispersion occurs at

microwave frequency. The microwave region provides meaningful information about

self association, solute-solvent and solute-solute type of molecular association among

polar molecules due to behavior of dielectric relaxation in liquid and solvents.

Relaxation mechanism associated with absorption of energy consequently involves in

reorientation of different groups in a molecule. Researchers have applied Frequency

Domain Techniques to study the relaxation behavior. Some of references are as

follows.

Tom Sidney Moore et al has been reported molecular interaction in terms of

hydrogen bonding and determine the equilibrium constants of acid and base in

solution using alkyl ammonium with hydroxyl ions. They worked to test the

applicability of method for determining equilibrium constants of a pseudo acids and

pseudo bases in solution [1].

K.V.Gopala Krishna have been reported a method to determine dipole moment

and relaxation time of polar substances from microwave measurements.

Method uses polar substances in non polar solvents, based as a function of


30

concentration. The advantage over other is eliminating determination of

density of solution and even concentration of the solute need not be determined [2].

W.M.Heston et al have been reported desirability of measuring selected

molecules in dilute solution in a variety of different solvents. An experimental method

called Voltage standing wave ratio for dielectric loss measurement for relaxation time

are employed [3].

Wendell M. Latimer et al have reported strong and weak electrolytes,

solubility of salts and the formation of complex ions in solution. They showed that

their exit a property called electropositive or electronegative character and

explanation amounts to saying that hydrogen nucleus held between two constitutes a

weak bond. The ionizing between polar and non polar compounds is given in terms of

intermolecular force. He showed that non polar compound do not have high

melting point and dielectric constant is a measure of this type of “polarity” but has no

significance with regard to highly polar compounds [4].

F.H.Branin and C.P.Smyth have discussed the results of a systematic

investigation of dielectric dispersion and absorption in microwave region. They

discussed relation between complex dielectric constant and propagation constant of

EM wave with in medium with new interferometric methods for measuring

wavelength [5].

Keniti Higasi has done pioneering works on dielectric relaxation and

molecular structure of liquids. The new method was developed to find dielectric

relaxation time by using the frequency domain microwave techniques [6].

W.D Kumler has reported the dielectric constant of liquids is a function of

number of molecules per cc of dipole moment, the electronic and atomic


31

polarization and the interaction of the molecules with each other. A method has been

devised to determine effect of molecular interaction on the dielectric constants of

liquids. They confirmed that liquids that do not form bonds have normal dielectric

constants; those that form hydrogen bonds have abnormal dielectric constants [7].

Edwin R Fitzgerald et al estimated dielectric behavior of liquids, gels and

solids at frequency from 15 to 15000 cycles / sec. The variation of complex dielectric

constant with frequency and temperature for polyvinyl chloride combined with

dimethylthianthrene are determined. Apparent activation energy for dipole rotation is

determined as a function of pure plasticizer and low polymer. Their result shows the

relative importance of each type of rotation will depend on relative concentrations of

polymer, plasticizer and the magnitude of their permanent dipole moments [8].

W.F. Hassell et al reported new bridge method for microwave to determine

dipole moments and relaxation times by using microwave bridge apparatus. They

developed a new method. This method is mainly used for study of hydrogen bonding

to gain from relaxation time in different solvents. This method is used to

examining the nature of intermolecular complexes and dipolar interaction at different

concentration [9].

Bass.S.J et al. have been measured the static dielectric constant, Dielectric

relaxation for dimethylformaide, formaide, N-methylformaide, acetamide and

propionamide in the frequency range of 1 to 250Mc using transformer bridge method

and Guarded cell with coaxial cylindrical electrodes. They reported that the values for

formamide is significantly large then the dimethylformaide. The results are compared

with predictions from models of chain wise association by hydrogen bonding. [10].


32

T.J. Bhattacharya et al have reported the dielectric relaxation of chloroform

and benzophenone in n-heptane and of binary mixtures of chlorobenzene and

bromobenzene in Nujol They measured complex dielectric constants for various

concentrations, static dielectric constants and individual dispersions of the polar

constituents of the ternary mixture in solution in n-heptane at the same relative

concentrations. The results are explained in terms of hindering forces influencing

dipole rotation [11].

Y. Tanaka et al have measured effect of the dielectric character of a solvent on

pyridine using the dielectric loss measuring set with a liquid cell operating on 1Kc-

3Mc. The solvent on pyridine-catalyzed reaction is discussed in terms of the modified

Kirkwood's expression Their results shows hydrogen-bonding effect of in toluene-

dioxan and nitrobenzene-dioxan mixtures and suggest that activated complex or

transition state species proposed plays an important role for reaction in solvents [12].

Brian Morris et al have been studied dielectric properties of Linde molecular

sieve zeolite with a series of polar and non-polar adsorbents in the frequency range

5 Hz to 148 kHz using vacuum cell method. The results are analyzed on the basis of

apparent dipole moment, associated with the cation jump, which is obtained from

dielectric absorption parameters [13].

H. Block et al have reported dielectric relaxation of polymaleimide with

N-alkyl, N-aryl polymaleimides in the frequency range 10−5 to 106 Hz using

microwave instrument. Their results shows three relaxations are observable and these

have been assigned to glass to rubber transition. Activation energies for these

processes are reported and thermal reactions demonstrated to affect the individual

relaxations [14].


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Shanmugasundaram and Meyyappan have reported the formation constants

and dipole moments of the complexes formed between acetone and methyl ethyl

ketone and phenol using dielectric microwave instruments. Their results indicated that

formation of 1:1 complex through hydrogen bonding of the type O-H⋅⋅⋅⋅O. The

formation constants obtained were in good agreement with values observed from

infrared studies of these mixtures [15].

Stockhausen and Manfred et al have been reported that complex permittivity

of mixtures of N-Methyl amide with methanol, ethanol, propan-1-ol and butan-1-ol

has been measured in the microwave frequency range from 20 MHz to 36 GHz at

20 °C using microwave measuring instrument. Their results are in terms of Debye

terms. The lower-frequency term are assumed to be due to self- and

hetero-association, while the other term is presumably due to the non-associated part

of the liquid [16].

Marie-Agnès Rix-Montel et al has been studied the interaction between DNA

and the oligopeptide lysine-tyrosine lysine (LTL) by a dielectric method. Their result

shows the comparison between conductivities of alone and of the complex LTL-DNA

allows showing an electrostatic interaction between LTL and phosphates sites of

DNA. Their result shows the existence of electrostatic interactions between and

oligopeptide and DNA [17].

K. Sen Gupta et al has been studied the dielectric absorption in 1-phenyl-

propyl of bromide, mercaptan and amine in the liquid state at different frequencies by

using microwave instrument. Their result shows the dielectric data were analyzed in

terms of molecular and end-group relaxation time. Their heat of activation for three

liquids are 1.8 k C / mole, relative weight factors of three liquids are 0.8, 0.65 and


34

0.85 and dipole moments is 1.35 are 1.33D and 1.34D respectively have been

determined [18].

S.M. Khameshara et al have been estimated the static dielectric constant at

300 KHz, refractive index and dielectric constant at 9.945 GHz (X-band) for different

aniline in dilute solutions of benzene over a temperature range 25–55°C. They

calculated the dielectric relaxation time by Higasi, Koga and Nakamura method and

also measured the relaxation time. Their result shows a systematic decrease of

relaxation time with increase in temperature. The energy parameters and the factors

are determined from the Eyring's rate equations [19].

S.M. Khameshara et al have been measured the dielectric permittivity and

dielectric loss at 9.945 GHz using slotted line and short circuiting plunger instrument

for 2-chloro-6-methylaniline, 3-chloro-2-methylaniline, 2-chloro-4-methyl-aniline, 4-

chloro-2-methyl-aniline and 5-chloro-2-methyl-aniline in various solvents. The static

permittivity at 300 KHz and free energies of activation and dipole moment of the

substituted anilines in different solvents are also determined. The data are analyzed by

Higasi's method .The values of relaxation time, distribution parameter (α) are

measured. This has been interpreted in terms of the intra molecular rotations of the

amino group occurring simultaneously with the overall molecular orientation. The

discrepancies are explained in terms of solute solvent interaction [20].

Shanmugasundaram and Mohan have reported the formation constant of

hydroxyl - carbonyl (methanol and n-butanol with acetone, methyl ethyl ketone,

cyclohexanone, ethyl acetate and amyl acetate) systems from the dielectric studies

using dielectric instruments. From their results, it has been noticed that the formation

constant values varied with the acidity and basics of the alcohols and carbonyl

compounds [21].


35

S.M. Khameshara et al have been reported the permittivity and dielectric loss

for different aniline substitute at four micro wave frequencies using short circuited

movable plunger instrument and optical frequency at 35°C in benzene solution. The

results are calculated using Cole -Cole method and the relaxation time for

intra molecular rotation for these suggest that the amino-group relaxes by an inversion

mechanism. The dipole moments evaluated by the microwave method are also

reported. It varies from 2.08 for 2 chloro 6 mehtyl aniline to 2.95D for 4 chloro 2

methyl aniline in benzene solution at 350C [22].

E. Jakusek et al have carried out the dielectric relaxation measurement in the

frequency range of 100 MHz-38 GHz using coaxial slotted lines instrument for

monoacetylferrocene in p-xylene by varying a concentration from 0 to 3% by weight.

Their results show that behavior of acetylferrocene in different temperature and

concentration conform closely dielectric dispersions to a single relaxation time. They

reported that under these conditions no intermolecular association or interaction of

any type was observed between the solute molecules [23].

Mridula Gupta et al have measured the dielectric relaxation for NH---N

bonded complexes of pyrrole and indole with pyridine and quinoline molecules at 9.8

GHz frequency. Using methods like Gopalakrishna, Higasi and Higasi, Koga and

Nakamura. The observed results indicate the presence of NH---N bonded complexes

under the microwave field. The dipole moments associated with the complexes have

been determined. The results obtained exhibit formation of NH---N bond, which

behave as a single unit under the applied field. Their result also supported by the

approximate additive nature of the relaxation times of the complexes [24].

Shanmugasundaram and Mohan have estimated dielectric constants and

dipole moment of the n-butanol-ketone (acetone and acetophenone) mixtures in CCl4


36

at 303 K using microwave dielectric instruments. They have reported the existence of

formation of 1:1 complex between n-butanol-ketone and carbon tetrachloride [25].

Aradhana et al have studied the dielectric constant of phenothiazine-iodine

system in benzene at a radiofrequency of 1MHz at 300C and 400C by using a dipole

meter instruments. They have reported that 1:1 molecular complex are formed

between donor-acceptor and extent of molecular association decreases with increase

temperature. It is shown that phenothiazines are good donors and possibility of

molecular association with iodine is due to active site atom in each donor [26].

Misra et al have studied the hydrogen bonded complex for acetate substitutes

with o-cresol in carbon tetrachloride using microwave bench instrument. They have

reported equilibrium constant, dielectric parameters and thermodynamic parameters

for the association process as well as dielectric relaxation process for ternary mixtures

are greater than that of binary mixtures [27].

Mulay et al. have carried out dielectric measurement for ethyl and butyl

acetates with m-cresol in benzene at 300 K using microwave instrument. They

reported a weak hydrogen bond between hydroxyl group and oxygen group of acetate.

Experimental data shows the high value of dipole moment for the above mixture and

it is due to a comparatively large chain length and inductive effect [28].

B.B. Swain et al. have reported dielectric constant for binary mixture of

butanol substitutes in benzene, carbon tetrachloride, and n-heptane using radio

frequency instrument and Eyring’s interaction parameter. The data has been utilized

for calculation of mutual correlation factor between unlike molecules. Their resultant

data are used to contribution of the unlike molecules to the excess free energy of


37

mixing and excess entropy. They reported the solute - solvent interactions are found

to be influenced by nature of the solvent [29].

H.D.Purohit et al. have been measured the permittivity and dielectric loss of

benzotrifluoride and benzotrichloride in benzene and decal in solution at four

microwave frequencies using microwave instrument at different frequency. They

reported relaxation times for overall rotation and group rotation and from their result,

they found relaxation times for overall rotation dependent on viscosity and relaxation

times for group rotation are found to independent of viscosity for the binary mixture.

Dipole moments of compounds in both benzene and decal in have been reported [30].

Chhavi Aggarwal et al. have studied dielectric measurement at 9.93 GHz

frequency using slotted line and short circuiting plunger instrument for 2, 3 and 4

bromo, 3 chloro anisole in various non-polar solvents. The static permittivity and high

frequency limiting permittivity are reported. Their results have been interpreted in

terms of intra molecular rotation of methoxy group, simultaneously with the overall

molecular orientation. They calculated free energy of activation for the dielectric

relaxation and viscous flow. They suggest presence of solute solvent interactions [31].

Dhar et al. have measured dielectric constant, refractive index and viscosity

for o-cresol with ethylene di-amine and tri ethylamine systems at different

temperatures using microwave frequency measuring instrument. The result shows

dielectric constant, refractive index and viscosity increased with increasing

concentration of o-cresol and reverse trend was noticed for different temperature [32].

John G et al. measured dielectric relaxation for a 3-bromopentane in

3-methylpentane in the frequency range from 100 kHz to below 1 μHz microwave


38

frequency instrument. The measurements reported mixtures yield a better fit to

Kohlrausch-Williams-Watts function [33].

R. Buchner et al. measured the Complex permittivity of methanol-tetra

chloromethane mixtures at 25°C. They reported concentration depend of relaxation

times and dispersion amplitudes reveal hydrogen bonding between the methanol’s

molecules as the dominating type of interaction. From observation three dispersion

steps for all spectra suggests that no major changes in the relaxation mechanism of

methanol induced in the studied mixture range on dilution with polar component [34].

Tripathy et al. have estimated the linear correlation factor for dilute solutions

of binary mixtures of alcohols with some amines in three non-polar solvents at 301 K

frequency domain instrument. From result they noticed in alcohol mixture value of

linear correlation factor increases while in amine mixture it decreases, this is because

of difference in hydrogen bonding of two groups. It was shown the correlation factor

increased in the alcohol-rich region and it is decreased to a low positive value in the

mixture containing amine rich region [35].

Dash and Swain et al have measured dielectric constant, mutual correlation

factor, excess molar polarization and excess free energy of mixing of tri-n-butyl

phosphate with primary alcohols at 455 kHz with temperature 302 K using frequency

domain instrument. The corresponding data are tabulated and they reported variation

of this parameters depend on chain-length of the alcohols [36].

V. Satheesh et al. have reported relaxation times and Kirkwood correlation

factor for mixtures allyl alcohol with pyridine, l, 4-dioxane and in benzene at 9.8 GHz

using single frequency dielectric measurements instrument. The dielectric data are

analyzed in terms of separate relaxation times. From observed value they noticed the


39

strength of hydrogen bond in OH-N Bridge is greater than OH-O Bridge. The

increment dipole moment values due to complex formation in all three cases because

of polarization interaction [37].

Abd-El-Nour et al. have investigated dielectric relaxation between some

N-Substituted maleimides and methyl methacrylate in Carbon tetrachloride and

benzene at different concentrations in the microwave region using sweep frequency

spectrometer instrument. The data were analyzed using Debye terms. The equilibrium

constant of association processes is studied by means of dielectric polarizations. They

reported there is a deviation in the data, due to some sort of molecular interaction

takes place between donors and acceptors. A linear correlation between the relaxation

time and solvent viscosity was noticed [38].

Dash et al have been measured the dielectric constant of Tri-n-butyl

phosphate in binary mixtures with five primary alcohols using frequency domain

instrument. Their result shows variation of dielectric parameters is mainly dependence

on chain-length of alcohols indicating 1-heptanol to be an efficient modifier and

complex was due to partial proton transfer and complex formation were

maximum in 1-heptanol system [39].

Turky et al have been reported dielectric loss in the frequency range

200 MHz-10 GHz have been measured in three mixtures and static permittivity for the

mixture of N, N-Dimethylformamide with 1-hexanol at different concentrations.

Static permittivity was measured using a dipole meter at a frequency of 2 MHz and

the dielectric loss was measured using a microwave swept frequency transmission

spectrometer. Result shows relaxation time increases with concentration related to

association process. The variation of static permittivity and dielectric loss as a


40

function of concentration indicated a solute solvent type of molecular association and

their result shows molecular association is maxima at 1:1 ratio [40].

David S Pearson et al have reported brief overview of different approaches to

dielectric analysis and highlight the potential role of this technology in the

characterization of lyophilized materials and in particular for proteins. They reported

use of dielectric analysis to help pharmaceutical scientists to optimize preservation of

therapeutic agents by freeze drying to be realized fully [41].

Ajay Chaudhari et al have studied the dielectric relaxation for tetra hydro

furan (THF) has been carried out in methanol and ethanol at different temperatures

using Time domain Reflectometry in frequency range of 10 MHz to 10 GHz. The

investigation shows the systematic change in dielectric parameters with change in

concentration and temperature. It is observed from their result that interaction in the

methanol-THF system is stronger than interaction in the ethanol THF systems [42].

Eid et al. have reported activation energy for the mixtures of 1-alcohols with

cyclohexane at different concentrations of alcohol. The static permittivity measured at

2 MHz using dipole meter and dielectric properties were determined at frequencies

ranging between 2 MHz and 36 GHz. The apparent dipole moment are increase with

increasing density of dipoles after passing through a minimum, shows the formation

of small associates with reduced polarity possible due to a ring like structure. Their

results show increase of activation energy with the chain length of alcohols and seem

to be the indicative of steric hindrance of intermolecular hydrogen bonding [43].

Hanna et al. have studied dielectric relaxation of ternary mixtures of different

diols and different alcohols in cyclohexane. Static permittivity was measured using

dipole meter with 2 MHz and frequency transmission spectrometer was utilized to


41

measure dielectric loss in frequency range 0.1-18 GHz. Their result shows dipole

moment and relaxation time increases with chain length of alcohols and diols.

Relaxation times are low for systems due to close position of two OH-groups [44].

U.S. Mohapatra et al. have investigated the dipole moment for hydrogen

bonded complexes of butanol with chlorobenzene in benzene at 455 kHz at 303.16 K

using dielectric measurement. The dielectric parameter like dipole moment,

interaction dipole moment and induced polarization for geometry of 1:1 complexs

were determined. Their results showed 1:1 complex formation was predominant in

these systems and hydrogen complexion was due to charge redistribution effect [45].

R.J Sengwa et al. have reported dielectric complex permittivity of propylene

glycol and poly (propylene glycol) were measured in the frequency range 10 MHz–4

GHz at 25°C using time domain reflectometry. The relaxation is described by a single

relaxation time using Debye model. They discussed particularly with respect to the

solvent behavior, which can be assigned to unaffected, loosely affected and tightly

bound solvent and also with respect to the propylene glycol chain coiling [46].

Kalamse and Nimkar have calculated the dielectric relaxation time, dipole

moment and thermodynamic parameters for diethylene triamine and ethane diol in

1,4-dioxane solution at different concentrations using x band microwave bench at

10.7 GHz. Their result shows the non linear variation of parameter with the change in

mole fraction and found the presence of solute-solute molecular association [47].

U.S. Mohapatra et al. have carried out the dielectric measurement for butanol

with aniline and pyridine separately at radio frequency of 455 kHz at 303K. The

dipole moment, inter dipole moment and induced polarization for the most favored

geometry of 1:1 complex in systems were evaluated from bond angle data. These


42

results are revealed the existence of 1:1 H-bonded molecular complexes in the

systems and polarization effect dominated in all the complexes [48].

M. Malathi et al have been reported the dielectric constants and dielectric

losses of acetanilide and acetamide in 1, 4-dioxan/benzene using x band microwave

bench instrument at 308 K. The activation energies, relaxation time for the over all

rotation and for the group rotation of molecules were determined using Higasi’s

method. Their result shows relaxation time of amides in non-polar solvent. They

proposed existence of solute–solvent and solute–solute molecular association [49].

Sampathkumar et al. have measured the dielectric parameter for 2,6-diphenyl-

4-piperidone with methanol, n-butanol, p-cresol and p-chlorophenol in benzene in for

different concentration using dielectric absorption technique. They reported that

relaxation time in present study range between 9 ps to 12 ps and the ternary system is

greater than binary mixture. They showed that relaxation time of proton increase as

acceptor increases in solvent environment and show the solute-solute interaction [50].

B S Narwade et al have reported the dielectric constant and dielectric loss of

n-propyl alcohol, ethylenediamine and their binary mixtures for different mole

fractions using microwave frequency instrument at 165 GHz. They reported excess

square refractive index, viscosity and activation energy of viscous flow and this

parameter are used to estimate the value for dielectric parameter. These parameters

have been used to explain the formation of complexes in the system [51].

M. Malathi et al have reported the hydrogen bonded complex formed by

formamide and acetamide with phenols in 1, 4-dioxan. Dipole moment of the complex

was determined by using Huyskens method. Their results show lone pair electron of

amides is single acceptor to form hydrogen bond and proton acceptor abilities of the


43

two amides are almost the same. They reported that as acidity of phenols increases,

the dipolar increments also increase [52].

Narwade et al. have been reported dielectric constant, dielectric loss and

activation energy for binary mixtures of n-propyl alcohol with ethylenediamine with

different concentration are measured using microwave frequency instrument at 11·15

GHz. Their result shows a strong 1:1 complex formation between molecule of

n-propyl alcohol and ethylenediamine [53].

Acharya et al. have been studied interaction between acetylacetone and

primary alcohols using wave meter-oscillator at 455 KHz frequency at 303K. They

reported dielectric constant, mutual correlation factor, excess molar polarization and

excess free energy of binary mixtures. They measured dielectric measurement for di-

isobutyl ketone with primary alcohols. From there result they conform interaction is

maximum for 1-pentanol when compare with other systems and interaction for equal-

molar ratio is maximum. It is confirms higher chain alcohol has greater

donating proton ability for their study [54, 55].

T.Thenappan et al have reported the dipole moment of N, N-dimethyl

formamide with n-propanol, 2-propanol, n-butanol, 2-butanol, isobutyl alcohol,

tert-butanol, 2-pentanol, 1-octanol, benzyl alcohol and 1-decanol in benzene at 308 K

using x band microwave bench instrument. There result shows the dipole moment was

found to be smaller in the secondary alcohol than in the primary alcohol. Because of

hydroxyl group is increases from primary to secondary [56].

Sharma et al. have measure the dielectric relaxation of ethanol and tetra

methyl urea in benzene solutions at 9.83 GHz with different temperature range using

standing microwave bench instrument. They have reported solute-solute and


44

solute-solvent types of molecular association. It was shown that dielectric relaxation

process can be treated as the rate process like viscous flow process [57].

Dharmalingam et al. have been studied the dielectric relaxation of methyl,

ethyl and butyl methacrylates with primary alcohols using dielectric microwave

technique at 9.84 GHz at a temperature of 298K.Their results show association

between alcohol and ester is higher in 1:1 complex. Further they reported the free

hydroxyl group of the alcohols and esters plays an important role in determinations of

the strength of hydrogen bond formed [58].

T.Thenappan et al have been reported static dielectric constant, dielectric

constant at high frequency, Kirkwood correlation factors, Bruggeman dielectric factor

and excess permittivity for different acetate with propanoic acid using dielectric

microwave technique at various temperatures and concentrations. Their results shows

existence of intermolecular interaction through hydrogen bonding between mixture

and dielectric parameters shows change with concentration [59].

K. Ramachandran et al have measured the dielectric relaxation of alcohol

amides substitute’s binary mixtures at different concentrations using time domain

reflectometry. The Kirkwood correlation factor and excess inverse relaxation time

were determined and discussed to yield information on the molecular structure and

dynamics of the mixture. The results shows solute-solvent interaction existed between

alcohols and amides [60].

Sengwa R J et al have been reported the static dielectric constant for the

binary mixtures of substitutes of N-methyl amide using x band microwave instrument

at 303 K. The Kirkwood correlation factor values of amide–amide mixtures were


45

determined from static dielectric constant. Their results show a strong hydrogen bond

interaction between molecules of amide–amide and 1:1 complexes are formed [61].

F. Liakath Ali Khan et al have studied the dielectric absorption of methyl and

butyl methacrylate with phenols in carbon tetrachloride using microwave frequency

instrument at 9.37 GHz at 308K. Their result shows the single frequency equation for

multiple relaxation times is function of the hydrogen bonding strength of phenolic

hydrogen, whereas the group rotation relaxation time is a function of the steric

interaction of proton donor [62].

S. D. Chavan et al have measured the dielectric complex permittivity using

microwave frequency instrument at the frequency range 10MHz – 20 GHz in

water-diol mixture. Their result shows the dielectric parameter and confirm the

intermolecular homogeneous and heterogeneous hydrogen bonding vary significantly

with the increase in concentration of the constituents of the diol-water mixtures [63].

G.M. Dharne Aruna et al have measured the dielectric relaxation of allyl

chloride with ethanol using x band micro wave instrument at frequency range of

10MHz – 20 GHz at 308K. They calculated the static permittivity, dielectric constant

at high frequency and relaxation time through dielectric measurements. The

Kirkwood correlation factor, excess static permittivity, and excess Inverse relaxation

time were determined and discussed to yield information for the intermolecular

interactions and dynamics of the system [64].

Amit Ron et al have reported the analysis of dielectric complex permittivity of

living biological cell suspended in a physiological medium using dielectric

spectroscopy. Their results show the polarization relaxation response of cells to


46

external electric field as function of the excitation frequency and this response is

strongly affected by both structural and molecular properties of cells [65].

A N Prajapati et al have measured the complex permittivity of fluoro benzene

with methanol at a frequency of 9.1 to 19.61 GHz using standard microwave bench.

They calculated the Kirkwood correlation factor, Bruggeman parameter and

interpreted the results in terms of molecular interaction between different molecular

species of the liquid mixtures [66].

C. K Mishra et a1 have studied the dielectric relaxation time of Ortho, meta,

para tolualdehyde and cuminaldehyde at different temperatures in benzenes

using frequency domain instrument. They have reported the intra molecular rotations

and the dipole relaxation are co-operative process and suggested that the solid rotator

phase exists on solidification. The conformed the interaction is due to intra molecular

rotations and the dipole relaxation [67].

2.2 Infra-Red spectroscopes

The association donor acceptor type bonding is very significant for the studies

of hydrogen bonding interaction and especially for the determination of free energy

and equilibrium constant. It gives rich source of information about hydrogen bonded

systems and H-bonded complexes. Fourier Transform Infrared (FTIR) spectroscopic

theoretical and experimental aspects of molecular association processes have been

discussed by several reviews.

This section is intended to provide information about previous studies

associated with Hydrogen bonding studies with the infrared spectroscopic

methods.


47

Chandra and Basu et al have reported that the equilibrium constants of

hydrogen bonded complexes of some carbonyls with different alcohols have been

measured from ultraviolet measurements. Their result shows the equilibrium

constants have been found to increase in the order: primary to tertiary, which indicates

that the primary alcohols have higher proton donating ability than other alcohols [68].

E.D. Goddard et al have reported that, the interaction between long chain

alcohols and sodiumsulfave by using spectroscopic method. From their result the

molecular association is shown to be strongest when the alcohol possesses a straight

hydrocarbon chain and it can be weakened considerably by altering the configuration

of the chain [69].

Charles M. Huggins et al reported the infrared measurements of stretching and

bending motions of chloroform in various solvents. There result is a correlation

between apparent intensity of band and the extent of interaction in the same solvent.

The band is very intense in triethylamine. No large change in the intensity of the

bending motion was observed. The spectral properties of chloroform-d are interpreted

to indicate molecular interactions similar to hydrogen bonding interactions [70].

Kagarise and Whetsel et al have estimated the hydrogen bonding interactions

of ethyl acetate, ethyl trichloroacetate and ethyl trifiuoroacetate with ethanol in

n-hexane were studied by using infrared spectroscopy. The results show the strength

of the interaction is increase as proton-accepting ability increase. This indicates that

the electronegative substituent’s of ethyl acetate reducing the proton-accepting ability

of carbonyl oxygen [71].

Rosenberg and Smith have reported the equilibrium constants for alcohols

with esters in n-tridecane using infrared spectroscopy. They observed the equilibrium


48

constants of t-pentyl alcohol less than other alcohol, the result shows the strength of

H-bond varies with the chain-length of alcohols and esters [72].

Smith and Rosenberg have been found the equilibrium constant for hexyl

hexanoate with 1-octanol in carbon tetrachloride using infrared spectroscopy. Their

result shows the equilibrium constant decreases with increasing temperature. This is

due to increase in kinetic energy of the molecules to break the hydrogen bonding in

the system [73].

J.W. Verhoeven et al have studied inter and intra molecular donor-acceptor

interactions. Their results show the intra molecular Charge Transfer

interaction between Donor and Acceptor [74].

Becker et al have reported the equilibrium constants for the 1:1 hydrogen

bonding systems involving the donors and acceptors in CCl4 solution by infrared

spectroscopic method. Their results show the substitution at the carbonyl carbon

reduces the proton-donating capability (acidity) in the expected order:

methanol, ethanol and t-butanol and the equilibrium constants were found to be

decrease [75].

Findlay and Kidman have calculated the enthalpy of hydrogen bonding

interaction for pyridine with primary alcohol using infrared spectroscopic

measurements. The results indicate that the strength of hydrogen bonding interaction

is high in propan-1-ol when compare with others [76].

Sassa and Katayama have reported the formation constants and excess Gibbs

free energies of the complexes formed between alcohols and proton acceptors

(acetonitrile, ethyl acetate, ethyl ether, acetone, pyridine and triethylamine) from the

infrared measurements, It was found that the spectroscopic information is useful to

obtain the non-ideal behavior of vapor-liquid equilibrium for systems [77].


49

Yu.I. Mitchenko et al have reported the molecular interaction in polymeric

amide-salt solutions using NMR, IR spectroscopic method. It has been shown from

their result that interaction occurs between the dipole of the ion pair .The polymer's

amide group leads to polarization of the macromolecule and causes interaction

between the planar groups of polymer chain with solvent molecules [78].

Ye.G Atovmyan et al have carried out infrared spectroscopic experiment to

find molecular interaction in the range of bond-stretching vibrations of the N-H bond

in oligobutadiene urethane. They measured the different thermodynamic parameter

for NH group transmission from the Free State into a complex of NH states and

reported the molecular interaction exists in the mixture [79].

I Shimada et al have carried out Fourier transform infrared spectroscopy

to study the molecular interaction between gramicidin D and bi layer membranes. The

result shows, presence of gramicidin in the membrane causes an increase in the

mobility of the alkyl chain and also a decrease in the abruptness of the transition [80].

Somnath Ganguly et al have reported the hydrogen bonding interactions of

heptanoic acid and octadecenoic acid in carbon tetrachloride. Their result shows

Intermolecular hydrogen bonding increases with increasing acid concentration. The

maximum amount of acid required to coat the particles decreases with increasing

chain length of the acid. Reported the amine interacts strongly with the ions on the

salt surface and hydrogen bonds with other amine molecules to cover [81, 82].

Jagdeesh Bandekar et al have reported that polyurethanes containing different

hard segments using Fourier-transform-infrared-attenuated total internal reflectance.

Their results shows that the existence of hydrogen-bonding interactions between the

C=O=C groups and the NH groups [83].


50

T.I. Titova et al have studied the molecular interactions between silica –

triethylamine (TEA) systems by Fourier transform infrared spectroscopy. They

reported that low-frequency shift of the wavelength of hydroxyl band is slight,

moderate and strong H-bonding of silanol groups to TEA molecules was found to

correlate with a high-frequency shift [84].

Zofia Dega-Szafran et al have carried out X-ray and Fourier transform

infrared studies of hydrogen bonds in some of pyridines with trifluoroacetic acid

complexes. The IR spectra with Nujol show a continuous absorption, whose intensity

decreases with elongation of the H-bond length [85].

Paola Sassi et al have carried out the Fourier transform infrared spectroscopic

study of dynamic and structural properties of 1-octanol as a function of temperature.

The results of the experiment clarify the characteristics of both internal and

external structure of 1-octanol and showed the strong relationship between structure

and dynamic in H-bonded liquid [86].

Klaus-Jochen Eichhorn et al have estimated the interactions between the

di block copolymer poly(styrene-b-4-vinylpyridine) P(S4VP) and pentadecylphenol

were analyzed by infrared difference spectroscopy and temperature-dependent Fourier

transform infrared spectroscopy. Their result shows the strong hydrogen bonding was

found between diblock copolymer P(S4VP) with amphiphile. They reported that

interaction leads to stable polymeric complexes and mesomorphic structures [87]

Krishnamurthy Ramachandran et al reported the hydrogen bonding

interactions between N-methylformamide with primary, secondary and tertiary

alcohols using FTIR spectroscopic method. From the measured data they reported that

most likely association complex formed between alcohol and N-methylformamide is

the 1:1 stoichiometric and complex formed between the hydroxyl group of alcohol


51

and the carbonyl group of N-methylformamide. The results showed proton donating

ability of the alcohols decreased in the order tertiary, secondary and primary [88].

P. Sivagurunathan et al have reported that the association between alcohols

and N,N-dimethylacetamide in carbon tetrachloride has been investigated using FTIR

spectroscopy at 298 K. The formation constants for 1:1 and 1:2 complexes were

calculated. Their result shows the formation constant and values of free energy

change increased with the increase in the chain length of alcohols and degree of

complex formation varied with the length of the carbon chain of alcohols [89].

Dharmalingam K.et al carried out the measurement of molecular interaction

between primary alcohols with ethyl methacrylate in n-heptane, CCl4 and benzene at

298 K using FTIR spectroscopic. The result indicate the existence 1:1 complex

formation between the alcohol and ethyl methacrylate and alkyl chain length of

alcohol and the solvent used play a significant role in the strength of hydrogen bond.

Also the strength and the nature of interaction between the molecules of 1-pentanol

with esters and acrylic esters have been discussed [90, 91].

Juffernbruch and Perkampus have investigated the association equilibrium of

the dibenzacridine and different OH- donors in CCl4, n-heptane, toluene and benzene

as solvents by Uv-Vis spectroscopic methods. They concluded that the nature of the

solvents plays a significant role in the formation of hydrogen bond [92].

Faria et al. have evaluated the formation constant of the hydrogen-bonded

complexes for substituted phenols with substituted esters in carbon tetrachloride

solution from infrared spectroscopic method. It has been found that the formation

constants depend on the electronic properties of the substituent’s within both the

hydrogen donor and acceptor molecules [93].


52

B.A. Shainyan et al have reported that the intra-molecular hydrogen bonds

interaction between sulfonamide derivatives of oxamide with di-thiooxamide using by

infrared spectroscopy method. Their result shows that the atoms-in-molecules of

donor–acceptor interactions are in good agreement with each other [94].

Adam Huczyński et al have reported the structural investigation of a new

complex of N-allylamide of Monensin (M-AM2) with a strontium per chlorate has

been studied by X-ray crystallography and FTIR spectroscopy. The results show there

is interaction between M-AM2 molecules due to additionally tie by an intra molecular

hydrogen-bonded chain. The FT-IR spectral and semi empirical calculations show

that the oxygen atom of the amide group is not involved in the coordination of the

cation [95].

Kuc et al. have determined the formation constants and free enthalpies of 1:1

and 2:1 hydrogen-bonded complexes formed between 2, 4, 6-trichlorophenol and

triethylamine in various solvents using infrared spectroscopic method. The formation

constants and free enthalpies suggested the specific solute-solvent interaction between

the hydroxyl group of phenol and the solvent molecules [96].

Zheng et al. have reported the infrared spectra of methyl methacrylate in CCl4

binary solvent systems. From their result they have been suggested that the hydrogen

bond exist between the carbonyl groups of methyl methacrylate and the proton of the

ethanol [97].

Munoz et al. have made infrared spectral study to analyze the hydrogen

bonding interactions between 1-methylindole with the alcohols in hexane. Their study

provided evidences on the existence of 1:1 hydrogen bonded complexes between the

hydroxyl group of alcohols and the π-electrons in the indole ring [98].


53

Tonge et al. have measured the enthalpy and entropy of hydrogen bond

formation betweenα, β-unsaturated esters and the hydrogen bond donors in CCl4 from

the FTIR studies. The enthalpy and entropy variations were linearly correlated to the

acidity of the proton donor and the basic of the proton acceptor, respectively [99].

Saito ST et al have reported Fourier transform infrared spectroscopy and

absorption spectra were used to determine the structural features, the binding mode

and the association constants for the emodin with DNA in aqueous solution. Their

result shows the emodin interaction occurs preferably via adenine and thymine base

pairs and also weakly with the phosphate backbone of the DNA double helix [100].

2.3 Ultrasonic study

Ultrasonic velocity and absorption measurements in liquids and liquid

mixtures find extensive application to study the nature of intermolecular forces. An

excellent review of work carried out on large number of liquid mixtures. As the

present studies deals with ultrasonic velocity and absorption studies pertaining to

binary, ternary liquid mixtures of organic liquids, substitute of amide and substitutes

of amine, a brief review of the relevant literature is given below.

Kaulgud et al measured ultrasonic velocity and adiabatic compressibility’s of

binary mixtures of acetonitrile, nitromethane, acetone-carbon in benzene and carbon

tetrachloride at different concentrations. They observed the adiabatic compressibility

decreases as ultrasonic velocity increases and ultrasonic velocity and adiabatic

compressibility decrease with increase in concentration for acetone and acetonitrile.

These have been explained on the basis of thermo dynamical excess functions and

variation of intermolecular free length for the mixtures [101].


54

Singh et al have been measured the densities and ultrasonic velocities at 30°C

in ternary liquid mixtures of acetonitrile with carbon tetrachloride-n-butanol and

dioxane-cyclohexane-chloroform. The increase in free length in the solutions due to

the mixing results in lowering of the velocity. From the study it was concluded that

the free length was a predominant factor in determining the nature of variation of

sound velocity. It has been further concluded that the dipole-dipole and hydrogen

bonding forces between unlike components make a negative contribution [102].

Francis E. Fox et al have reported that theory of the ultrasonic interferometer

can be adapted to determine the ultrasonic velocity for liquid media. The result shows

the measurements at 2.79 and 8.37 megacycles yield the "frequency-free"

coefficient of absorption in water approximately 19×10-17 while the coefficient of

reflection varies from 0.7 to 0.9 at boundary surfaces of monel metal and brass [103].

Adgaonkar et al reported ultrasonic velocities and adiabatic compressibility in

binary liquid mixtures of aniline, quinoline and pyridine with phenol. It is observed

from their result that at the molar ratio 1:1, the velocity and compressibility showed

discontinuity. These discontinuities have been attributed to complex formation

through hydrogen bonding and decrease in adiabatic compressibility indicates a

decrease in free volume at the discontinuities [104].

E.J. Williams et al has study rotational isomerism of tertiary amines using

ultrasonic relaxation. The ultrasonic studies have been carried out on a number of

tri-n-alkylamines and substituted triethylamines in the liquid phase. The sound

absorption data have been analyzed to yield barrier heights between rotamers. They

concluded entropy of the higher energy isomer decreases with decreasing temperature

presumably as the rotation of the methyl groups become more restricted [105].


55

J K Das et al have reported that the ultrasonic velocity in binary mixture of

MIBK with eight aliphatic alcohols using ultrasonic interferometer at a frequency

2MHz with temperature of 303K. The excess properties like isotropic compressibility,

molar compressibility, inter molecular free length; available volume and acoustic

impedance are calculated by using measured data. The result shows variation of

parameter due to interaction and it is dependent upon chain length of alcohols [106].

G. Venkata Ramana et al have measured ultrasonic velocities in dilute

solutions of water in diethylamine, triethylamine, dibutylamine and di-sec-butylamine

have been determined at 298.15 K using ultrasonic interferometer at 3MHz. The

results shows linear variation of ultrasonic velocities explained as water molecules as

monomer in the solution and non linear variation has been explained in water-water

and water amine interactions, this leading to the formation of complexes [107].

AN. Kannappan et al have reported the molecular Interaction of h-bonded

Complexes of Benzamide with Propan-2-ol, Butan-1-ol,1-Pentanol and n-Hexanal in

1,4-Dioxan using ultrasonic method. Acoustic parameter adiabatic compressibility,

free length, free volume, internal pressure, viscous relaxation and Gibbs free energy

were evaluated by measured value. They reported the nature of molecular interaction.

There results support occurrence of complex formation through intermolecular

hydrogen bonding in ternary liquid mixtures [108].

Rita Mehra et al have studied the variation of sound speed for diethyl amine

and 1-Decanol using ultrasonic interferometer at 2MHz .They reported measured

sound speed, density, viscosity and derived parameters like acoustic impedance,

internal pressure and molecular interaction parameter for diethyl amine at all three

temperature. The interpretation of excess parameters is given by Positive value of


56

interaction parameter and they conforms the intermolecular interaction between

diethyl amine and 1-Decanol [109].

Gyan P. Dubey et al has been measured experimental values of densities and

speeds of sound for different temperature and viscosities at 298 K in the binary

mixtures of 1-octanol in n-hexane, n-octane, and n-decane and their binary mixtures

were measured by ultrasonic method. They reported the negative values viscosity

deviation decreases in the following sequence: n-hexane > n-octane > n-decane. The

experimental and calculated quantities are used to study nature of mixture [110].

Uvarani. R et al have reported the molecular interaction in cyclohexanone

with o-cresol and p-cresol at 303k using ultrasonic velocity measured at a frequency

of 2MHz by using ultrasonic interferometer. They measured ultrasonic velocity,

density, viscosity and acoustical parameters. It is observed from their results that as

the concentration of cyclohexanone increases the ultrasonic velocity decreases for

both the systems. They used the excess parameter for the interpretation of nature and

strength of the interactions in these binary systems [111].

Thirumaran.S et al have reported the ultrasonic velocity, density and viscosity

have been measured for the liquid mixtures of cresols with N, N-Dimethyl formamide

in CCl4 at 303, 308 and 313 K. The acoustical parameters such as adiabatic

compressibility, free length, free volume, internal pressure, acoustic impedance and

molar volume are calculated from the experimental data. Their result shows the

density; viscosity and ultrasonic velocity increase with increasing molar concentration

of cresols and conformed due to increasing values of acoustic impedance supports the

possibility of molecular interactions since H-bonding between mixture. The results

are interpreted in terms of molecular interactions in the mixtures [112].


57

C. Shanmuga Priya et al reported that the density, viscosity and ultrasonic

velocity have been measured for binary liquid mixtures containing

Methylmethacrylate with 2-Methoxy ethanol at 303K. The compressibility, free

length, free volume, internal pressure, relaxation time, acoustic impedance and

Gibbs’s free energy values have been calculated from the measured ultrasonic

parameters. These parameters are used to discuss the molecular interactions in the

mixtures and they reported there is a interaction in this mixture [113].

J. Udayaseelan et al have estimated the ultrasonic velocity, density and

viscosity of N,N Dimethylacetamide and N-Methylacetamide with Alkoxyethanols in

Carbon tetrachloride at 303, 313 and 323K ultrasonic interferometer of 2MHz

frequency. They reported the acoustical parameter are calculated and change in

parameter with reference to the nature of interaction between the component

molecules. From the obtained values, molecular interactions have been found through

hydrogen bonding between solute and solvent liquid mixtures [114].

A. N. Sonar et al has been reported the molecular interaction of substituted

acetone-water mixture at 303k by using ultrasonic interferometer at a frequency of

2MHz. From their results, it is observed that the variation of ultrasonic velocity

decreases with increase in percentage of acetone for all systems. It was found that,

the intermolecular free length increase due to greater force of interaction between

solute and solvent by forming hydrogen bonding. From result they show the

solute-solvent interaction exists between drugs and organic solvent mixture. [115].

Anbananthan et al carried out the ultrasonic velocity measurement in liquid

mixtures of dioxane with of alcohols with a view to studying molecular association in

these mixtures. The result shows the ultrasonic velocity and adiabatic

compressibility are depend on the concentration of the mixtures. They show


58

maximum for velocity and minimum for compressibility by varying concentration.

The minimum compressibility in these mixtures indicates complex formation through

hydrogen bonding [116].

Narayanasamy et al. measured excess volumes, isentropic compressibility’s in

the mixtures of acetonitrile in n-propanol, i-propanol, n-butanol, i-butanol, and

cyclohexanol at 300K using the ultrasonic interferometer. It is reported that, these

mixtures show positive excess volumes, and these excess volumes are attributed to

weak hydrogen bonding and there is a interaction in the mixture [117].

Dharmaraju et al have been measured the ultrasonic velocity of the mixtures

of acentonitrile with n-pentanol, n-heptanol, n-octanol at 303K. Their result shows a

weak interaction between acentonitrile with heptanol. They reported that the excess

volume and excess compressibility increase with the chain length of alcohols [118].

M.V. Rathnam et al ultrasonic speeds of binary mixtures of methyl benzoate

with benzene, isopropyl benzene, isobutyl benzene, acetophenone, cyclopentanone,

cyclohexanone or 3-pentanone including those of pure liquids were measured. Their

result shows the formation of molecular interaction in the binary mixtures [119].

Thanuja B et al have been measured the density, ultrasonic velocity for the

4-methoxy benzoin with ethanol, chloroform, acetonitrile, benzene, and di-oxane

mixture measured using ultrasonic method at 298 K. They reported intermolecular

interaction created between solute–solvent and polarity of the solvent is discussed.

From the above data, ultrasonic parameters and excess parameters have been

calculated. These parameters were used to study the nature and extent of

intermolecular interactions between component molecules in mixtures [120].


59

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