ultrasonic velocities, relative permittivities and refractive indices for binary liquid mixtures of...

$: Ultrasonic velocities, relative permittivities and refractive indices for binary liquid mixtures of trichloroethene with pyridine and quinoline$
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ELSEVIER Fluid Phase Equilibria 109 (1995) 39-51

Ultrasonic velocities, relative permittivities and refractive indices for binary liquid mixtures of trichloroethene with pyridine and quinoline

Jagan Nath

Chemistry Department, Gorakhpur University, Gorakhpur 273009, India

Received 15 December 1994; accepted 21 February 1995

Abstract

Ultrasonic velocities, u, relative permittivities, E, and refractive indices, n, have been measured for binary liquid mixtures of trichloroethene (CHC1CCI 2) with pyridine (CsHsN) and quinoline (C9H7N) at 303.15 K. The relative-permittivity data have been used to calculate total molar polarisations, P, for the various systems. The quantities Ak s and Ap which refer, respectively, to the deviations of the isentropic compressibilities and total molar polarisations of the mixtures from the values arising from the mole fraction mixture law, have been calculated. The apparent molar polarisations, PD, of CsHsN and C9HTN have also been calculated in CHCICC12. The values of Aks, AP and PD show that CHC1CCI 2 forms intermolecular complexes with CsH5N and C9H7N in the liquid state. The values of the equilibrium constant, K e, for the formation of 1:1 complexes of CHCICCI z with CsHsN and C9H7 N, as calculated using relative permittivity data, are in accord with the theory based upon electrostatic interactions of the solute with the liquid.

Keywords: Experimental; Ultrasonic velocity; Permittivity; Refractive index; Binary liquid mixtures; Trichloroethylene; Pyridine; Quinoline; Complex formation

1. Introduction

Binary systems of trichloroethene (CHC1CC1 e) with pyridine (CsHsN) and quinoline (C9HTN) are of considerable interest from the viewpoint of the electron donor-acceptor interactions leading to the formation of intermolecular adducts between the components in the liquid state. The specific interactions of CsHsN and C9H7N with CHC1CC12 can be visualized as being due to the presence of lone pair of electrons on the nitrogen atom of CsHsN and C9U7N which can act as n-donors towards CHCICC12. On the other hand, CHCICCI 2 can act as o'-acceptor towards, and form hydrogen bonds with CsHsN and C9H7N. Although binary systems of CHC1CC12 with aromatic hydrocarbons which can act as 7r-donors, and with oxygen-containing compounds 1,4-dioxane, acetone, methylethylketone and anisole which can act as n-donors due to the presence of oxygen atom, have been thoroughly investigated (Nath and Dubey, 1980; Nath and Dixit, 1985; Nath and Saini, 1989, Nath and Saini, 1990; Nath and Rashmi, 1990a, Nath and Rashmi, 1990b; Nath et al., 1991; Nath et al., 1994), extensive studies of binary systems of CHCICCI 2 with nitrogen-containing components have not been

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40 J. Nath / Fluid Phase Equilibria 109 (1995) 39-51

Table 1 Values of the densities, p, and the refractive indices, n, of the various components at 303.15 K

Liquid p (g cm -3) n

This work Literature This work Literature values a,b values a,b

Trichloroethene 1.45148 1.4514 1.4715 1.4718

Pyridine 0.97284 0.97281 1.5040 1.50466 Quinoline 1.08582 1.08579 1.6225 1.6222

a Riddick and Bunger (1970); b Timmermans (1950).

reported. Hence, in the present programme, the study of the binary systems of CHCICCI 2 with CsHsN and C 9 H 7 N is undertaken and the measurements of ultrasonic velocities, refractive indices, and the relative permittivities have been made for these systems at 303.15 K, and the results obtained are interpreted in this paper.

2. Experimental

Quinoline (Fluka, AG) of AR quality was fractionally distilled under reduced pressure and was stored in dark coloured bottles. Pyridine (SDS) of HPLC quality was used without further purification. Trichloroethene (SRL) of AR quality was shaken with potassium carbonate solution, washed several times with water, dried over anhydrous potassium carbonate, and then fractionally distilled. The densities of the purified samples of CHC1CC12, C 9 H 7 N and CsHsN measured at 303.15 _ 0.01 K are compared with the available data (Timmermans, 1950; Riddick and Bunger, 1970) in Table 1 which shows that there is good agreement between the two sets of values.

The ultrasonic velocities, u, in pure liquids and binary mixtures, were measured with an accuracy of ___ 1.0 m s -1, at 303.15 _ 0.01 K and at frequency of 3 MHz, using a multifrequency ultrasonic interferometer (Mittal Enterprises, New Delhi). The isentropic compressibilities, ks, were calculated from the relation

X1VI* q'-X2V2* -I- V E

ks= u2(XlM1 +X2M2) (1)

where X a and X z are the mole fractions of the components 1 and 2, respectively, in the mixture, and M 1 and M 2 are the molecular weights, and VI* and V2* are the liquid molar volumes, of the pure components designated 1 and 2, and V E is the excess molar volume of the mixture. Values of VI* and V2* needed to calculate k S from Eq. (1) were obtained from the present values of densities, p, for CHC1CCI2, CsHsN and CgH7N reported in Table 1, whereas the values of V E for CHCICCI 2 + C5HsN and CHC1CC12 + C9H7 N, at the desired mole fractions were obtained at 303.15 K, by interpolation of the values of V E at the corresponding mole fractions at 298.15 and 308.15 K, as obtained by using the constants of Redlich-Kister type equation reported earlier (Nath and Srivastava, 1986).

The values of k s are accurate to _+ 1.0 TPa-1. The relative permittivities, e, were measured at a frequency of 1.8 MHz and at 303.15 + 0.01 K, with a dekameter (type DK03, Wissenschaftlich-Tech-

J. Nath / Fluid Phase Equilibria 109 (1995) 39-51 41

nische Werkst~itten, Germany), using cells calibrated with liquids of known (Lange, 1973) relative permittivity: cell MFL l / s , no. 2078 for mixtures having • < 7.0, and cell MFL 2/S, no. 2084 for mixtures having • > 7,0. The precision in • is ca. 0.005 units for mixtures having higher concentrations of CHC1CCI 2 in C9H7N and CsHsN, and ca. 0.01 units for mixtures having lower concentrations of CHC1CC12.

Measurements of refractive indices, n, were made at 303.15_ 0.01 K, with an accuracy of +0.0002 units, using a thermostatted Abbe refractometer. The values of n were obtained for sodium-D light.

3. Results and discussion

The values of u and k~ for the pure liquids CHC1CCI 2, CsHsN and C9H7N , and for the binary mixtures of CHCICCI 2 with CsHsN and CqH7N at 303.15 K are given in Table 2. Values of u for the mixtures of CHCICC12 with CsHsN and C9H7N have been plotted against mole fraction of CHC1CCI2, X1, in Fig. 1. The present values of u and k s for CHCICCI 2 and C9H7N are in excellent agreement with the corresponding values reported earlier (Nath and Saini, 1990; Nath and Tevari, 1992). The present experimental values of • for CHC1CC12, CsHsN and C9H7 N, and for binary mixtures of CHC1CCI 2 with C5HsN and C9H7 N at 303.15 K are reported in Table 3. Values of • for the binary mixtures of CHC1CC12 with CsHsN and C9H7N have been plotted against the mole fraction of CHCICC12, X1, in Fig. 2. The present values of • for CHCICC12 and C9H7 N at 303.15 K, are in good agreement with the data reported earlier (Nath and Dubey, 1980; Nath and Tevari, 1992). The present values of n for CHCICCI 2, C9H7N and CsHsN are compared with the available data (Timmermans, 1950; Riddick and Bunger, 1970) in Table 1. The experimental values of n for binary mixtures of CHCICCI 2 with CsH5N and C9H7N at 303.15 K are reported in Table 4. The values of u for mixtures of CHCICC12 with CsHsN and CqH7N have been fitted by the method of least squares to the polynomial (Iglesias et al., 1994) equation

u =A o +A1X 1 +AzX12 + A 3 X3 (2)

The values of the constants A0, Aa, A 2 and A 3 of Eq. (2), along with the standard deviations 8(u) are given in Table 5. The values of n for mixtures of CHC1CCI 2 with CsH5N and C9H7N have been fitted by the method of least squares to the polynomial (Iglesias et al., 1994) equation

n = a + bX 1 + cX 2 + dX 3 (3)

The values of the constants a, b, c and d of Eq. (3), along with the standard deviations 6(n) , for the two systems are listed in Table 6.

The values of k~ (see Table 2) for the mixtures of CHC1CCI 2 with CsHsN and C9H7N , as obtained from Eq. (1) have been fitted by the method of least-squares to the equation

ks = Xlks l -~- X2ks2 -~- X lX2[ Oo -~- Ol( X l - X2 l -~- O2( Xl - X2) 2] (4)

where X 1 and X z are the mole fractions of CHC1CC12 and the second component respectively in the mixtures, ks~ and ks2 are the isentropic compressibilities of the two pure components, and B 0, B 1 and B 2 are constants characteristic of a system. Values of B o, B 1 and B2, along with the standard deviations 6 ( k s) are given in Table 7. The values of the quantity Ak s which refers to the deviations


Table 2 Values of u and k s for the systems of CHCICC12 with CsHsN and C9HTN at 303.15 K

u k s X 1 (ms- I) (TFa- 1 )

CHCICCI 2 + CsHsN 0.0000 1399 525 0.0638 1363 535 0.1156 1335 543 0.1651 1309 551 0.1903 1297 554 0.2122 1286 558 0.2606 1265 564 0.2947 1250 569 0.3338 1233 575 0.3680 1218 580 0.4058 1204 585 0.4442 1188 591 0.4899 1170 598 0.5101 1164 600 0.5616 1145 608 0.5865 1137 611 0.6303 1122 617 0.6665 1110 623 0.7072 1097 628 0.7512 1083 635 0.7935 1071 640 0.8324 1060 646 0.8713 1049 651 0.9114 1038 657 0.9520 1027 663 1.0000 1015 669 CHC1CC12 +C9H7N 0.0000 1547 385 0.0742 1511 395 0.1560 1471 408 0.2191 1437 420 0.2765 1408 430 0.3456 1373 444 0.5176 1280 486 0.5822 1245 504 0.6422 1213 521 0.7272 1165 551 0.7673 1143 566 0.8433 1101 597 0.9104 1063 626 0.9516 1042 644 1.0000 1015 669

f rom rec t i l i nea r d e p e n d e n c e o f k S o f the m i x t u r e on m o l e f rac t ion , and w h i c h c o r r e s p o n d to

A k S = X 1 X 2 [ B o + B 1 ( X 1 - X 2) + B 2 ( X 1 - ) ( 2 ) z ], m a y be c o n s i d e r e d to be in t e rp re t ed in t e r m s o f the

s t r eng th o f i n t e rac t ions o p e r a t i n g b e t w e e n the c o m p o n e n t s o f a sys t em. The n e g a t i v e v a l u e s o f A k s

J. Nath // Fluid Phase Equilibria 109 (1995) 39-51

1600/l- I , I i

43

1400

1200

1100

100C

t | I I I L 0.0 0.2 0.4 0. g 0.8 1.0

2C 1

Fig. 1. Plot of u against mole fraction of CHCICCI2, X1, for the various systems at 303.15 K: O, CHC1CC12 + C9HTN; [] CHC1CC12 + CsHsN.

for a given system may be visualized as due to a closer approach of unlike molecules, leading to reduction in volume and compressibility. The various types of interactions which operate between components of different systems are: dispersion forces which should make a positive contribution to Aks, and charge-transfer, hydrogen bonding, dipole-induced dipole and dipole-dipole interactions which should make negative contributions to Ak s. Dispersion forces are operative in all systems, and for a given system in which more than one type of interaction are present between the components, the values of Ak s would be the net result of the contributions from all types of interaction.

The present data show that the values of Ak s are very slightly positive for CHCICC12 + CsHsN , and highly negative for CHCICCI 2 + C9H7N. This suggests the likelihood of the formation of intermolecular complexes of CHC1CCI 2 with C9HTN and CsHsN in the liquid state.

It has been pointed out (Earp and Glasstone, 1935) that the apparent molar polarisation of the various components in binary liquid mixtures give conclusive evidence concerning the formation of intermolecular complexes between the components. The apparent molar polarisations can be obtained from the molar polarisation of pure components and those of their binary mixtures. The molar polarisations are calculated from the relative-permittivity and refractive-index data on pure components and their binary mixtures. Hence, in order to get conclusive evidence concerning the formation of intermolecular complexes of CHCICCI 2 with CsHsN and C9H7N in the liquid state, the values of the molar dielectric polarisation, P, have been calculated for CHC1CCI 2 + CsHsN and CHCICC12 + C9HTN , using the Kirkwood-Fr6hlich equation (Moreau and Douh6ret, 1976):

(e - n2)(2e + n2)Vm P = (5)


Table 3 Relative permittivities, ~, for the various systems of CHC1CCI 2 at 303.15 K

X 1 E

CHC1CC12 + CsHsN 0.0000 12.17 0.0661 11.60 0.1045 11.25 0.1342 10.99 0.2043 10.36 0.2396 10.08 0.2758 9.76 0.3452 9.16 0.4270 8.43 0.4971 7.86 0.5234 7.64 0.5769 7.19 0.6876 6.328 0.7215 6.044 0.7965 5.418 0.8468 4.883 0.8730 4.665 0.9315 4.050 1.0000 3.335 CHCICC12 + C9H7N 0.0000 8.98 0.0848 8.75 0.1684 8.51 0.2654 8.12 0.3773 7.63 0.4976 6.99 0.5739 6.622 0.6949 6.010 0.7094 5.890 0.7589 5.470 0.8318 4.963 0.8748 4.580 0.9365 3.965 0.9794 3.539 1.0000 3.335

where V m is the liquid molar volume. The densities reported in this paper were used to calculate the values of V m for the pure liquids CHC1CC12, CsHsN and C9HTN for use in Eq. (5), whereas the molar volumes of the binary mixtures of CHC1CCI 2 with CsHsN and C9H7 N were obtained from the molar volumes of the pure liquids and the data on excess volumes reported earlier (Nath and Srivastava, 1986). The values of the total molar polarisations, P , for mixtures have been used to calculate the quantity Ap (see Fig. 3), which refers to the deviations of the molar polarisations of the mixtures from the values arising from the mole-fraction mixture law, using the relation

A p = p - X ~ P 1 - X 2 P 2 (6)

J. Nath / Fluid Phase Equilibria 109 (1995) 39-51

I l I I I

45

11.0

10.0

9.0(

8.0

7.0

6,0

5.0

t,J~

I I i I I

0.0 0.2 O.t. 0.6 0.8 1.0

Fig. 2. Plot of e against the mole fraction of CHC1CCI 2, X 1, for the various systems at 303.15 K: O , CHC1CCI 2 + C9H7N; Fq, CHC1CC12 + CsHsN.

where P1 and P2 are the total molar polarisations of the pure components 1 and 2 respectively. Fig. 3 shows that the values of Ap are highly positive for CHCICCI 2 + CsHsN and CHC1CCI 2 + C9H7N , thus suggesting the likelihood of the formation of strong complexes of CHC1CCI 2 with CsHsN and C9H7N in the liquid state. The total molar polarisations were used to calculate the apparent molar polarisations, PD, of CsHsN and C9H7N at various concentrations throughout the whole range of composition in CHCICCI2, by following the method described by Earp and Glasstone (1935). Values of PD were found to increase sharply with decreasing mole fraction of CsHsN and C9H7N in the systems CHCICC12 + CsHsN and CHC1CC12 + C9H7N respectively. A typical plot showing the variation of PD of CsHsN with its mole fraction, X2, is given in Fig. 4. This behavior of Po of CsHsN and C9H7N in the systems CHC1CCI 2 + CsHsN and CHC1CCI 2 + C9H7N , indicates the likelihood of the formation of complexes of CHC1CCI 2 with CsHsN and C9H7N in the liquid state. Considering that 1:1 molecular complex (AD) of the trichloroethene (A) with the two above-men- tioned nitrogen-containing compounds (D) is formed, the molar polarisation, PAD, of the molecular complex AD was calculated using the procedure described by Earp and Glasstone (1935). Values of PAD for 1:1 complexes of CHCICCI 2 with CsHsN and C9H7N are 283.5 and 299.2 cm 3 mo1-1,


Table 4 Values of n for the various systems of CHCICC12 at 303.15 K

X a n

CHC1CC12 + C s H s N 0.0000 1.5040 0.0312 1.5024 0.0708 1.5012 0.1133 1.4995 0.1340 1.4985 0.2690 1.4948 0.3532 1.4920 0.4444 1.4892 0.5305 1.4872 0.6714 1.4830 0.7783 1.4795 0.8363 1.4775 0.9221 1.4746 1.0000 1.4715

CHCICCI 2 + C 9 H 7 N 0.0000 1.6225 0.2127 1.6010 0.2693 1.5940 0.3250 1.5868 0.4134 1.5745 0.5335 1.5565 0.5884 1.5475 0.6794 1.5330 0.7389 1.5220 0.8386 1.5042 0.9029 1.4915 0.9500 1.4820 1.0000 1.4715

Table 5 Values of the constants Ao, AI, A 2 and A 3 of Eq. (2), and the standard deviations 6(u) for the systems of CHC1CC12 with CsHsN and CgH7N at 303.15 K

system A o A 1 A e A 3 ~(u) ( m s - 1) ( m s - 1 ) (ms - 1) ( m s - l) ( m s - 1)

CHCICC12 + C s H s N 1398.41 - 577.16 264.02 - 70.83 0.59 CHCICC12 + C9H7N 1546.96 - 478.63 - 90.22 36.62 0.69

Table 6 Values of the constants a, b, c, and d of Eq. (3), and the standard deviations 6(n) for the systems of CHCICCI 2 with C s H s N and C9H7N at 303.15 K

system a b c d 6(n)

CHC1CC12 + C s H s N 1.50379 - 0.03989 0.024495 - 0.016944 0.0002 CHCICC1 e + C9H7N 1.62264 - 0.08876 - 0.06888 0.00681 0.0003


Table 7 Values of the constants B 0, B 1 and B 2 of Eq. (4), and the standard deviations t$(k s) for the systems of CHCICC12 with

CsHsN and C9HTN at 303.15 K

System B o n 1 B~ ~(k s) (TPa- 1 ) (TPa- 1 ) (TPa - 1 ) (TPa- ' )

CHC1CCI 2 + C5HsN 6.66 - 1.17 10.99 0.42 CHCICCI 2 + C9H7 N - 182.71 - 4 1 . 4 0 - 13.95 0.62

E

U

I

2O

10 o

o i~ ra

%° o

I 0.0 0.2

I i I

% o

o o o ta°tto o

13 O

I I I 0.~ O.G 0.8 1.0

Fig. 3. Plot of Ap against the mole fraction of CHCICC12, X 1 , for the various systems at 303.15 K: (3, CHCICC12 + CgH7N; n , CHC1CC12 + CsHsN.

260 e - ,-~ E

u

24C

22C

20C

0.0 ! I I I

0.2 0.4 O.G 0.8 1.0

I i i I

:q

Fig. 4. Plot of the apparent molar polarisation of pyridine, PD, VS. its mole fraction, X 2, for CHC1CCI 2 + CsHsN at 303.15 K.

4 8 J. Nath // Fluid Phase Equilibria 109 (1995) 39-51

O.G

0 .2

c .o

o.o

o

E - 0 . 2

~ - 0 . 4 o

-0 .6

- 0 . ~

--1 .I]

I I I # I

0

0

0

I I I I 1 0.10 0.12 0.1/" 0.1 6 0.1 B

Fig. 5. Plot of log [Kf (mole fraction)-1] against f(•) for CHC1CCI 2 d - C 5 H 5 N at 303.15 K.

respectively. The equilibrium constant, Kf, for the formation of 1:1 complexes of CHCICC12 with CsHsN and C9H7N has also been calculated, by the method of Earp and Glasstone (1935). Kf shows a significant variation with composition for CHCICC12 + CsHsN and CHC1CC12 + C9HTN. Rivail and Thiebaut (1974) have found that for the pure binary system CHC13 + CsHsN, Kf exhibits a significant variation with composition. As pointed by Rivail and Thiebaut (1974), a theory based upon the electrostatic interactions of the solute with the liquid predicts a linear variation of the logarithm of Kf with the quantity

( e - 1 ) ( ~ - 1) = ( 7 )

3 ( 2 , + ~ )

where ~ is the infinite-frequency relative permittivity of the mixture. In the present programme, the values of ~ for use to calculate f (e ) from Eq. (7), were obtained from ~ = n 2. Fig. 5 and 6 show that there is a linear variation of log K e with f (e ) for CHC1CC12 + CsHsN and CHC1CC12 + C9H7N , respectively, suggesting that the values of K e calculated from the data on e and n, using simple approach of Earp and Glasstone (1935), are in accord with the theory based upon the electrostatic interactions of the solute with the liquid. The values of K e (see Fig. 5 and Fig. 6) show that the specific interactions of CHCICCI 2 with CsHsN and C9HTN are of comparable magnitude.

The specific interaction of CHC1CCI 2 with CsHsN and C9H7N can be considered to be due to the formation of hydrogen bonds between the components on account of interaction of H atom of CHCICC12 with the electron cloud on the nitrogen atom of CsHsN and C9HTN. There is, however,


I I I ! I

0.4

0.2 O t i , ¢ -

.~ 0.0 U

-0.2 o

E

i "J -0.4 o

-0.6

-0.8

l I I I I I o,~o o.~z o 1~ o .~s o ,is o.zo

(~)

Fig. 6. Plot of log [Kf (mole fraction)-l] against f (e) for CHC1CCI 2 4-C9 HvN at 303.15 K.

also a possibility of the formation of charge-transfer complexes of CHCICCI 2 with CsHsN and C 9 H 7 N due to interaction of chlorine atoms of CHCICC12 with the lone pair of electrons of the nitrogen atom of CsHsN and C9H7N.

4. List of symbols

a,b,c,d Ao,A1,A2,A 3

B o , B 1 , B 2

E

E~

Kf k~ Aks

M1 Me n

6(n)

P P1 P2 PAD

Constants of a polynomial expansion fitting the refractive index data for mixtures Constants of a polynomial expansion fitting the data on ultrasonic velocities of mixtures Constants of Redlich-Kister type equation fitting the values of Ak s Relative permittivity Infinite-frequency relative permittivity = ( e - 1)(G - 1)/3(2 e + ~ ) Equilibrium constant for the formation of 1:1 complex Isentropic compressibility Deviation of the isentropic compressibility of the mixture from the value arising from the mole fraction mixture law Standard deviation in k s Molecular weight of component 1 Molecular weight of component 2 Refractive index Standard deviation in the values of n from those obtained from the polynomial equation Molar polarisation Molar polarisation of Component 1 Molar polarisation of Component 2 Molar polarisation of 1:1 complex AD

50

PD AP

P u

Vm v,*

X1

- 1 m s TPa -1

J. Nath / Fluid Phase Equilibria 109 (1995) 39-51

Apparent molar polarisation of the donor component Deviation in the molar polarisation of the mixture from the value arising from the mole fraction mixture law Density Ultrasonic velocity Molar volume Liquid molar volume of component 1 Liquid molar volume of component 2 Mole fraction of component 1 Mole fraction of component 2 meter per second (Tera pascal)- 1

Acknowledgements

I am highly thankful to the Head of the Chemistry Department, Gorakhpur University, Gorakhpur, for providing laboratory facilities. Thanks are also due to the Council of Scientific and Industrial Research, New Delhi, for financial support.

References

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Nath, J. and Tevari, M., 1992. Ultrasonic and dielectric behaviour of binary systems of quinoline with methylene chloride, chloroform, carbon tetrachloride, benzene and cyclohexane, J. Chem. Soc. Faraday Trans., 88: 2197-2202.

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