Ultrasonic study of n-alkanols in toluene with nitrobenzene

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1 Indian Journal of Pure & Applied Physics Vol. 47, April 2009, pp Ultrasonic study of n-alkanols in toluene with nitrobenzene S Thirumaran* & J Earnest Jayakumar *Department of Physics, D D E Annamalai University, Annamalainagar thiru_phymaran@yahoo.co.in Received 21 April 2008; revised 29 December 2008; accepted 7 January 2009 The ultrasonic velocity, density and viscosity of the mixtures of the n alkanols, namely, 1 propanol, 1 butanol, and 1 pentanol in toluene with nitrobenzene at 303 K have been measured. From the measured data of ultrasonic velocity, density and viscosity, some of the acoustical parameters such as adiabatic compressibility (β), free length (L f ), free volume (V f ) and internal pressure (π i ) have been measured. The excess values of the above parameters are also evaluated. The results have been analysed and interpreted in terms of molecular interactions such as dipole-dipole interaction through hydrogen bonding between nitrobenzene and 1-alkanols, and donor-acceptor complexity observed between toluene and nitro-benzene molecules. Keywords: Adiabatic compressibility, Free length, Free volume, Internal pressure, Hydrogen-bonding, Dipole-dipole interactions 1 Introduction Ultrasonic investigations of liquid mixtures consisting of polar and non-polar components are considerable importance in understanding intermolecular interactions between the component molecules and find applications in several industrial and technological processes 1-2. Such studies as functions of concentration are useful in giving insight into the structure and bonding of associated molecular complexes and other molecular processes. The variation of ultrasonic velocity and other ultrasonic parameters along with their excess values of binary or ternary liquid mixtures with changing mole fraction of one of the components has been investigated by many researchers 3-4. The study of molecular association in organic ternary mixtures having alcohol as one of the components is of particular interest, since alcohols are strongly self-associated liquids having a three dimensional network of hydrogen bond 5 and can be associated with any of other group having some degree of polar attractions 6.. Although several investigations 7-9 were carried out in liquid mixtures having alcohol as one of the components, a systematic study in a series of primary alcohols in ternary systems has been scarcely reported. The ultrasonic velocity data for ternary liquid mixtures has been studied by many researchers However, no effort appears to have been made to collect the ultrasonic velocity data for the ternary mixtures of nitrobenzene, toluene with 1-alcohols. In the present study, the molecular interactions in the systems nitro-benzene + toluene + 1-propanol + 1- butanol and 1-pentanol at 303 K have been characterized. The addition of nitrobenzene which is non-associated and highly polar to the dissociated 14 alcohol molecules forms dipole-dipole interactions through hydrogen bonding and addition of toluene, a non-polar leads to the formation of complexation between itself and nitrobenzene molecules. 2 Materials and Methods The liquid mixtures of various concentrations in mole fraction were prepared by taking AR grade chemicals, which were purified by standard methods 15. In all systems, the mole fraction of the second component, toluene (X 2 = 0.4) was kept fixed while the mole fractions of the remaining two were varied from 0.0 to 0.6 so as to have the mixtures of different compositions. There is nothing significant on fixing the second component at X 2 = 0.4. The ultrasonic velocity in liquid mixtures have been measured using an ultrasonic interferometer (Mittal type: Model: F81) working at frequency 2MHz with an overall accuracy of ± 0.1 ms 1. The density and viscosity are measured using a Pyckno meter and an Ostwald s Viscometer with an accuracy of ± 0.1kg m 3 and ± m Nm 2 s, respectively. All the precautions were taken to minimise the possible experimental error. The set-up is checked for

2 266 INDIAN J PURE & APPL PHYS, VOL 47, APRIL 2009 standard liquids. The values obtained are compared with earlier values and found that they match very well with each other. 3 Theory Adiabatic compressibility has been calculated from the speed of sound (U) and the density (ρ) of the medium using the equation as : 1 = (1) U ρ β 2 Intermolecular free length has been determined as: L f = KT β (2) where K T is a Jacobson s constant. Suryanarayana 16 obtained a relation for free volume in terms of ultrasonic velocity (U) and the viscosity (η) of the liquid as: 3 / 2 M U eff V = (3) f Kη where M is the effective molecular weight eff ( M = Σm eff i x i, in which m i and x i are the molecular weight and the mole fraction of the individual constituents respectively). K is a temperature independent constant which is equal to for all liquids. On the basis of statistical thermodyanamics, Suryanarayana 17 derived an expression for the determination of internal pressure by the use of free volume concept as: 1/ 2 2 / 3 Kη = ρ π brt 7 / 6 (4) i U M eff where K is a constant, T the absolute temperature, η the viscosity in Nsm 2, U the ultrasonic velocity in ms 1, ρ the density in Kgm 3 and the effective molecular weight. M eff Excess value (A E ) has been calculated by using the relation A E where = A exp A... (5) id n A = A X, A is any acoustical i id i = 1 i i parameters and X i the mole fraction of the liquid component i. 4 Results and Discussion The present systems taken up for study are : I 1- propanol + toluene + nitro-benzene; II 1-butanol + toluene + nitro-benzene; III 1-pentanol + toluene + nitro-benzene The experimentally determined values of density (ρ), viscosity (η) and ultrasonic velocity (U) at 303K of all the pure components are listed in Table 1. The same values for the ternary liquid systems I III are presented in Table 2. Table 1 The values of density (ρ), viscosity (η) and velocity (U) of pure liquids at 303 K liquids density ρ/(kg/m 3 ) viscosity η/( 10-3 NSm -2 ) velocity U/(m/s) nitrobenzene toluene propanol butanol pentanol Table 2 The values of density (ρ), viscosity (η) and velocity (U) at 303 K for Systems I, II and III X 1 X 3 density ρ/(kg/m 3 ) viscosity η/( 10-3 NSm -2 ) System I: 1-propanol + toluene + nitro-benzene velocity U/(m/s) System II: 1-butanol + toluene + nitro-benzene System III: 1-pentanol + toluene + nitro-benzene

3 THIRUMARAN & JAYAKUMAR: ULTRASONIC STUDY ON N-ALKANOLS IN TOLUENE WITH NITROBENZENE 267 Table 3 The values of adiabatic compressibility (β), free length (L f ) free volume (V f ) and internal pressure (π i ) and their excess values at 303 K X 1 X 3 adiabatic compressibility β/( m 2 N -1 ) free length L f / ( m) free volume V f /( 10 7 m 3 mol 1 ) internal pressure π i /( 10 6 Nm 2 ) excess adiabatic compressibility β E / ( m 2 N -1 ) excess free length L f E / ( m) excess free volume V f E / ( 10 7 m 3 mol 1 ) excess internal pressure π i E /( 10 6 Nm 2 ) System I: 1-propanol + toluene + nitro-benzene System II: 1-butanol + toluene + nitro-benzene System III: 1-pentanol + toluene + nitro-benzene The values of adiabatic compressibility (β), free length (L f ), free volume (V f ), and internal pressure (π i ) and their excess values for three systems at 303K are given in Table 3. Fig.1 represents the variation of adiabatic compressibility (β) and excess adiabatic compressibility (β E ); free length (L f ) and excess free length (L f E ); free volume (V f ) and excess free volume (V f E ), and internal pressure (π I E ) and excess internal pressure (π I E ) with mole fraction of alkanols for system-i. Figs 2-3 represent the same excess values for systems II and III, respectively. In all the three ternary liquid systems, the ultrasonic velocity decreases with increasing concentration of 1-alkanols. This behaviour at such concentrations is different from the ideal mixtures behaviour and can be attributed to intermolecular interactions in the systems studied 16,17. The variation of ultrasonic velocity in a solution depends upon the increase (or) decrease of intermolecular free length after mixing the components. On the basis of a model, for sound propagation proposed by Eyring and Kincaid 20, ultrasonic velocity should decrease, if the intermolecular free length increase and vice-versa. This is infact observed in the present investigation for all the three liquid systems. As ultrasonic velocities of all the three liquid systems decrease with increasing mole fraction of primary alkanols, the adiabatic compressibility (β) and intermolecular free length (L f ) show the reverse trend. i.e., both the parameters found to increase.

4 268 INDIAN J PURE & APPL PHYS, VOL 47, APRIL 2009 Fig. 1 (a) Adiabatic compressibility (β), and its excess value (β E ); (b) Free length (L f), and its excess values (L f ); (c) Free volume (V f), and its excess values (V f E ); (d) Internal pressure ((π i), and its excess values ((π I E ) for System-I at 303K

5 THIRUMARAN & JAYAKUMAR: ULTRASONIC STUDY ON N-ALKANOLS IN TOLUENE WITH NITROBENZENE 269 Fig. 2 (a) Adiabatic compressibility (β), and its excess value (β E ); (b) Free length (L f), and its excess values (L f ); (c) Free volume (V f), and its excess values (V f E ); (d) Internal pressure ((π i), and its excess values ((π I E ) for System-II at 303K

6 270 INDIAN J PURE & APPL PHYS, VOL 47, APRIL 2009 Fig. 3 (a) Adiabatic compressibility (β), and its excess value (β E ); (b) Free length (L f), and its excess values (L f ); (c) Free volume (V f), and its excess values (V f E ); (d) Internal pressure ((π i), and its excess values ((π I E ) for System-III at 303K

7 THIRUMARAN & JAYAKUMAR: ULTRASONIC STUDY ON N-ALKANOLS IN TOLUENE WITH NITROBENZENE 271 The increase in adiabatic compressibility and intermolecular free length with increasing mole fraction of alkanols indicates significant interactions between nitrobenzene and alkanol molecules forming hydrogen bonding through dipole-dipole interaction. As alkanols are liquids which are associated through hydrogen bonding and in the pure state; they exhibit an equilibrium between multimer and monomer species. Further, when nitrobenzene is mixed with alkanols, the NO 2 group can interact with OH group. The aromatic derivatives set up on interaction between the π-electrons cloud and the hydroxyl group. This interaction is of minor intensity as compared with hydrogen bonding, but leads to formation of intermolecular complexes 21. The nitro-benzene which is relatively complex molecule and its non-ideality in all probability may be due to the polarity arisen out of C N and N O bonds. As ar as the contribution of nitro-group is concerned it rotates freely along the C N axis which is likely to give more flexibility to the interactions arising due to the two highly polar N O bonds 22. Also it may be explained by taking account of electron withdrawing capacity of NO 2 group which acts as an electron acceptor towards the π-electrons of toluene ring. This is due to the fact that CH 3 group of toluene is an electron donating group through induction, enhances the π-electron density of the toluene ring. This makes the donation of π-electrons (of toluene) for NO 2 group easier forming donor acceptor complex between toluene and nitrobenzene molecules 23. Thus, dipole-dipole interaction through hydrogen bonding between nitrobenzene and alkanols as well as donor acceptor complexation between toluene and nitrobenzene molecules clearly enhance the increase in adiabatic compressibility and intermolecular free length. Similar results were observed by earlier workers 24 in their liquid mixtures. Further, the decrease in free volume and increase in internal pressure with rise in concentration of alkanols in all the systems clearly show the increasing magnitude of interactions 25. In order to understand the nature of molecular interactions between the components of the liquid mixtures, it is of interest to discuss the same in terms of excess parameter rather than actual values. Non-ideal liquid mixtures show considerable deviation from linearity in their physical behaviour with respect to concentration and these have been interpreted as arising from the presence of strong or weak interactions. The effect of deviation depends upon the nature of the constituents and composition of the mixtures. In the present investigation, the excess values of adiabatic compressibility (β E ); excess free length (L f E ); excess free volume (V f E ), and excess internal pressure (π I E ) are negative in all the three systems over the entire range of composition. Sri Devi et al. 26 suggested that the negative excess values have been due to the closely packed molecules which account for existence of strong molecular interaction and positive excess values to weak interaction between unlike molecules. The sign of adiabatic compressibility (β E ) and excess free length (L f E ) play a vital role in assessing the compactness due to molecular interaction in liquid mixtures through charge transfer, dipole-dipole interactions 27, and dipole-induced dipole interactions interstitial accommodation and orientational ordering 28 leading to more compact structure-making, which enhances excess adiabatic compressibility (β E ) and excess free length (L f E ) to have negative values. The excess negative values of adiabatic compressibility (β E ) and excess free length (L f E ) in the present investigation is an indication of strong interaction in the liquid mixtures 29. The negative excess values of internal pressure in all the three systems clearly confirms this prediction. 5 Conclusions From ultrasonic velocity, related acoustical parameters and their excess values for the ternary liquid mixtures of 1-alkanols with nitrobenzene in toluene for various concentrations at 303K, it has been found that there exists a dipole-dipole interaction through hydrogen bonding between nitrobenzene and 1-alkanols. The donor acceptor complexation is observed between toluene and nitrobenzene molecules. Acknowledgement The authors are thankful to Dr. AN. Kannappan, Professor and Head, Department of Physics, Annamalai University for encouraging them. References 1 Amalandu Pal & Gurcharan Das, J Pure & Appi Ultrasonics, 21 (1990) 9. 2 Syal V K, Chauhan M S, Chandra B K & Chauhan S, J Pure & Appl Ultrasonics, 18 (1996) Oswet S L & Patel A J J Chem Eng Data, 40 (1995) 194.

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