IJPRD, 2014; Vol 6(10):December-2014 (005 - 014) International Standard Serial Number 0974 – 9446 -------------------------------------------------------------------------------------------------------------------------------------------------EXCESS VOLUMES, DEVIATION IN VISCOSITIES AND IR STUDIES OF O-DICHLOROBENZENE AND OCHLOROPHENOL WITH ACETONE, ACETOPHENONE, CYCLOHEXANONE AND CYCLOHEXANE V J NAUKUDKAR*1 and A. B. SAWANT2 1* Department of Chemistry, K. V. N. Naik, Arts, Commerce & Science College, Nashik, Nashik 422 002, Maharashtram, India 2 Department of Chemistry, M S G College, Malegaon Camp 423 105, Maharashtra, India Both college affiliated to Savitribai Phule Pune University. ABSTRACT The densities and viscosities of binary mixtures of odichlorobenzene and o-chlorophenol with acetone, acetophenone, cyclohexanone and cyclohexane have been measured at room temperature. These binary mixtures also studied by Infrared spectroscopy. The data have been utilized to compute the excess volumes, deviation in viscosities and correlate to Infrared spectroscopy. The results have been interpreted in terms of molecular interactions existing between the components of the mixtures. Keywords- Excess molar volume, Viscosity deviation, Infrared spectroscopy, o- Dichlorobenzene, o-Chlorophenol, Ketones, Cyclohexane, Molecular Interactions. Correspondence Author V J NAUKUDKAR Department of Chemistry, K. V. N. Naik, Arts, Commerce & Science College, Nashik, Nashik 422 002, Maharashtram, India Email: [email protected] INTRODUCTION The composition dependence of thermodynamic properties has proved to be very useful tools in understanding the nature and extent of pattern of molecular aggregation resulting from intermolecular interaction between components1, 2 . In the present paper binary liquid mixture of odichlorobenzene (ODB) and o-chlorophenol (OCP) with acetone (AC), acetophenone (AP), cyclohexanone (CYNO) and cyclohexane (CYN) have been studied. The thermodynamic and transport properties of o-dichlorobenzene (ODB) and ochlorophenol (OCP) with above ketones have been studied over the entire composition range at 298.15 K. Experimental The entire chemical used was of A. R. grade with purity >99% are used as such. The purity of liquid was checked by comparing experimental values of densities and viscosities of these liquids Available online on www.ijprd.com 5 International Journal of Pharmaceutical Research & Development with those reports in the literature (Table 1)3-9. Binary mixtures were prepared by mixing a known mass of each liquid in an airtight, stoppered glass bottle. The masses were recorded on digital balance (SHIMANZU AUX 220) to an accuracy of ± 1× 10-4g. The estimated error in mole fraction was < 1× 10-4. Care was taken to avoid contamination during mixing. For present study a specific gravity bottle10/single stem pycnometer11 was used for the density measurements. The specific gravity bottle was calibrated with freshly prepared triply distilled water. The density measurements for each experimental liquid were repeated three to four times. This procedure enabled us to get an uncertainty of ±5 x 10-4 gm/cm3 in density measurements. The density measurements for each experimental liquid were repeated at least three to four times and the results averaged. This procedure enabled us to get an uncertainty of ±0.0005 gm.cm-3 in density measurements. I.R. measurement through liquid mixtures provides an excellent tool to investigate inter and intramolecular interactions between like and unlike molecules. I.R. spectroscopy studies of pure and binary mixtures of ODB and OCP with ketones have been recorded over the whole composition range at room temperature and atmospheric pressure. ISSN: 0974 – 9446 Theory The excess molar volume (VE) can be computed from experimental density data using the relationship. VE = x1M1[1/ρm – 1/ρ1] + x2M2[1/ρm – 1/ρ2] Where, xi, Mi and ρ i designate the mole fraction, the molecular weight and the density of the component i. ρm is the density of mixture. The Ostwald viscometer was calibrated with triply distilled water at 298.15 K. A viscometer was selected having a flow time of approximately 100300 seconds at 298.15 K. The flow time measurement was repeated a number of times (usually 5-6 times). The difference reading did not deviate from the mean by more than 0.2s. To determine the influence of temperature on viscosity, the time of out flow was measured at 298.15 K. From the densities and times of flow, absolute viscosities of the liquid mixtures were calculated. Deviations in viscosities (∆η) were obtained as follows: ∆η = ηmix – (x1 η1 + x2 η2) (2) where η1 and η2 are the viscosities of pure components 1 and 2, respectively and ηmix is the viscosity of the liquid mixture. Table 1. Comparison of experimental data of ρ and η with literature at 298.15 K. Liquids ρ x 10-3 kg. m-3 Exp η x 103 kg. m-1. s-1 Lit 3 Exp Lit 1.326 1.3243 ODB 1.2995 1.3003 OCP AC AP 1.2577 1.25723 3.479 0.7846 0.78444 0.305 1.0231 1.02385 1.612 -0.30294 1. 6176 CYNO CYN 0.9423 0.94227 1.895 0.7737 0.77388 0.881 -0.8869 RESULTS AND DISCUSSION VE and ∆η studies: The derived parameter data VE and ∆η at the experimental temperamental are listed in Table 2 and 3.The density and viscosities for the binary mixtures of ODB with AC, AP, CYNO, and CYN are listed in Table 2 and OCP with AC, AP, CYNO, and CYN are listed in Table 3 at atmospheric pressure and at 298.15 K. Figures 1 to 4 exhibit the variation of VE/∆η of ODB/OCP with ketones at 298.15 K and atmospheric pressure. ODB + Ketones: From Figure (1), VE are negative for binaries ODB + AC, ODB + AP, ODB + CYNO, ODB + CYN at 298.15 K and atmospheric pressure over the Available online on www.ijprd.com 6 ( International Journal of Pharmaceutical Research & Development ISSN: 0974 – 9446 to the formation of weak molecular complexes, when compared to all remaining mixtures. entire range of composition. ODB + CYN for which the VE values are more negative, which may be due Excess Molar Volume Mole Fraction 0.00 -1.00 0.0 -2.00 -3.00 -4.00 -5.00 -6.00 -7.00 -8.00 -9.00 0.2 0.4 0.6 0.8 1.0 Figure 1. Variation of VE for for (x1) ODB + (1-x) AC (■), AP (X), CYNO (●) and CYN (■) at 298.15 K. values of ∆η generally follow the order: CYNO > AP. Figure (2) shows the variation in ∆η for The positive values of ∆η in these mixtures can be binaries ODB + AC, ODB + AP and ODB + CYNO at interpreted in terms of strong interactions 298.15 K. ODB + AC show negative deviation. ∆η between unlike molecules, ODB + CYNO and ODB + values shows negative due to dispersion forces are 12 AP. dominat . ODB + PN show positive deviation. ODB + CYNO and ODB + AP show positive deviation. The Table 2. ρ, η, VE and Δη of binary liquid mixture at 298.15 K. ρ x 10-3 η x 103 kg.m-3 kg.m-1.s-1 ODB(x1) + AC(1- x1) 0.0681 0.8334 0.378 0.1412 0.8880 0.434 0.2199 0.9420 0.491 0.3048 0.9953 0.552 0.3967 1.0479 0.624 0.4966 1.0995 0.709 0.6054 1.1496 0.817 0.7245 1.1994 0.938 0.8555 1.2484 1.086 ODB(x1) + AP(1- x1) 0.1033 1.0527 1.570 0.2058 1.0850 1.565 0.3076 1.1154 1.554 0.4086 1.1438 1.535 0.5090 1.1709 1.512 0.6086 1.1976 1.479 0.7075 1.2240 1.439 x1 VE x 106 Δη x 103 m3.mol-1 kg.m-1.s-1 -0.191 -0.439 -0.624 -0.738 -0.801 -0.780 -0.634 -0.468 -0.227 -0.030 -0.041 -0.056 -0.073 -0.085 -0.092 -0.084 -0.072 -0.044 -0.244 -0.756 -1.040 -1.105 -1.045 -0.943 -0.821 0.030 0.057 0.077 0.089 0.098 0.095 0.086 Available online on www.ijprd.com 7 International Journal of Pharmaceutical Research & Development 0.8057 1.2494 1.397 0.9032 1.2728 1.345 ODB(x1) + CYNO(1- x1) 0.0929 0.9848 1.992 0.1872 1.0267 1.942 0.2831 1.0678 1.886 0.3805 1.1082 1.827 0.4795 1.1436 1.763 0.5802 1.1775 1.690 0.6825 1.2096 1.613 0.7866 1.2414 1.525 0.8924 1.2704 1.400 ODB(x1) + CYN(1- x1) 0.0967 0.8349 0.888 0.1942 0.9080 0.916 0.2923 0.9779 0.946 0.3912 1.0467 0.979 0.4908 1.1128 1.019 0.5911 1.1727 1.064 0.6922 1.2185 1.111 0.7940 1.2553 1.159 0.8966 1.2742 1.214 ISSN: 0974 – 9446 -0.614 -0.240 0.075 0.053 -0.940 -1.546 -2.033 -2.431 -2.349 -2.125 -1.763 -1.378 -0.759 0.159 0.168 0.172 0.174 0.173 0.163 0.150 0.128 0.069 -1.500 -3.858 -5.546 -6.905 -7.865 -8.176 -7.263 -5.653 -2.603 -0.013 -0.023 -0.033 -0.040 -0.039 -0.035 -0.028 -0.020 -0.008 Table 3. ρ, η, VE and Δη of binary liquid mixtures at 298.15 K. x1 ρ x 10-3 η x 103 kg.m-3 kg.m-1.s-1 OCP(x1) + AC (1- x1) VE x 106 m3.mol-1 Δη x 103 kg.m-1.s-1 0.0746 0.8311 0.421 0.1535 0.8871 0.543 0.2371 0.9388 0.707 0.3260 0.9898 0.936 0.4204 1.0397 1.258 0.5211 1.0866 1.708 0.6286 1.1309 2.158 0.7437 1.1717 2.581 0.8672 1.2104 2.988 OCP(x1) + AP (1- x1) 0.1127 1.0507 2.098 0.2223 1.0834 2.540 0.3289 1.1156 3.043 0.4325 1.1408 3.566 0.5334 1.1618 4.100 0.6317 1.1815 4.323 0.7274 1.1992 4.273 0.8206 1.2164 4.145 0.9114 1.2334 3.598 OCP(x1) + CYNO (1- x1) -0.401 -1.167 -1.520 -1.807 -1.996 -1.949 -1.700 -1.177 -0.483 -0.158 -0.284 -0.382 -0.431 -0.405 -0.270 -0.158 -0.096 -0.075 -0.519 -1.535 -2.412 -2.554 -2.299 -1.945 -1.433 -0.901 -0.382 0.311 0.545 0.844 1.169 1.511 1.546 1.313 1.008 0.287 Available online on www.ijprd.com 8 International Journal of Pharmaceutical Research & Development 0.1028 0.9798 2.656 -0.850 0.2049 1.0188 3.393 -1.589 0.3064 1.0575 4.248 -2.250 0.4073 1.0949 5.064 -2.743 0.5076 1.1275 5.545 -2.796 0.6073 1.1576 5.560 -2.625 0.7064 1.1855 5.426 -2.290 0.8026 1.2104 4.958 -1.786 0.9027 1.2342 4.181 -1.107 OCP(x1) + CYN (1- x1) 0.1056 0.1056 0.1056 0.1056 0.2100 0.2100 0.2100 0.2100 0.3130 0.3130 0.3130 0.3130 0.4148 0.4148 0.4148 0.4148 0.5153 0.5153 0.5153 0.5153 0.6146 0.6146 0.6146 0.6146 0.7127 0.7127 0.7127 0.7127 0.8096 0.8096 0.8096 0.8096 0.9054 0.9054 0.9054 0.9054 ISSN: 0974 – 9446 0.598 1.173 1.867 2.524 2.846 2.702 2.411 1.792 0.855 0.1056 0.2100 0.3130 0.4148 0.5153 0.6146 0.7127 0.8096 0.9054 Deviation in Viscosity 0.20 0.15 0.10 0.05 0.00 -0.05 0.0 0.2 0.4 0.6 0.8 1.0 -0.10 -0.15 Mole Fraction Figure 2. Variation of ∆η for (x1) ODB + (1-x) CYNO (●), AP (X), CYN (■) and AC (■) at 298.15. OCP + Ketones: Figures (3) shows the variation in interaction takes place between a lone pair of E V for binaries OCP + AC, OCP + AP, OCP + CYNO, electrons of the oxygen atom of ketone and Cl, O-H OCP + CYN at 298.15 K. OCP + AC show less group14. This may also be due to the formation of negative deviation. The VE (x1 ≈ 0.5) shows the weak molecular complexes due change of free order: OCP + AC > OCP + AP > OCP + CYNO. OCP + volumes in the real mixture because of interstitial PN show less negative deviation and OCP + CYN accommodation of ketone molecules into cluster of shows more negative VE. OCP molecules. E Negative V reveals the existence of specific interaction between unlike molecules13. The Available online on www.ijprd.com 9 International Journal of Pharmaceutical Research & Development Mole Fraction Excess Molar Volume 0.00 -2.00 ISSN: 0974 – 9446 0.0 0.2 0.4 0.6 0.8 1.0 -4.00 -6.00 -8.00 -10.00 -12.00 -14.00 Figure 3. Variation of VE for (x1) OCP + (1-x) AC (■), AP (X), CYNO (●) and CYN (■) at 298.15 K. Figure (4) gives the variation of ∆η for binaries dominating.OCP + CYNO and OCP + AP show OCP + AC, OCP + AP, OCP + CYNO, OCP + CYN at positive deviation. The positive values of ∆η in these mixtures can be interpreted in terms of 298.15 K over the entire composition range. OCP + AC and OCP + CYN show negative deviation. ∆η strong interactions between unlike molecules, OCP values shows negative due to dispersion forces are + CYNO and OCP + AP. 4.00 3.00 Deviation in Viscosity 2.00 1.00 0.00 -1.00 0.0 0.2 0.4 0.6 0.8 1.0 Mole Fraction Figure 4. Variation of ∆η for (x1) OCP + (1-x) CYNO (●), AP (X), AC (■) and CYN (■) at 298.15 K. Infrared studies: observed at around 1680-1690 cm-1 due to The FTIR absorption frequencies of the binary conjugation effect. From Table 4.0, it is observed mixtures of ODB and OCP with ketones over the that C=O stretching frequency is almost same from x1 ≈ 0.1- 0.9 for ODB + AC, ODB + AP (fig.6) and entire range at room temperature are listed in Tables 4.0-6.0. ODB + CYNO. Lower C=O stretching frequency is ODB + Ketones: observed at x1 ≈ 0.1 and higher C=O stretching C=O stretching vibrations: The band due to frequency is observed at x1 ≈ 0.8 and 0.9 for all C=O stretching vibration is observed in the region systems. The frequency follows the order: ODB + 1650-1850 cm-1. For aliphatic ketone C=O AC > ODB + CYNO > OCP + CYNO > ODB + AP. -1 stretching vibration is at 1710-1720 cm and for OCP + Ketones: aromatic ketone C=O stretching vibration it is Available online on www.ijprd.com 10 International Journal of Pharmaceutical Research & Development C=O stretching vibrations: From Table 5.0, it is observed that C=O stretching frequency decreases from x1 ≈ 0.1 to 0.9 for OCP + AC, OCP + AP (fig.5) and OCP + CYNO. Higher C=O stretching ISSN: 0974 – 9446 frequency observed at x1 ≈ 0.1 and lower for all above systems except OCP + AC. The frequency follows the order: OCP + AC > OCP + CYNO > OCP + AP. Table 4. IR stretching frequencies of C=O (cm-1) in (x1) ODB and (1-x1) ketones systems. x1 0 ODB+AC 1714.6(w) ODB +AP 1683.7(s) ODB +CYNO 1710.7(s) 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 1714.6(w) 1714.6(w) 1714.6(w) 1714.6(w) 1714.6(w) 1714.6(s) 1714.6(s) 1714.6(s) 1714.6(m) 1714.6(w) 1683.7(s) 1683.7(s) 1683.7(s) 1683.7(s) 1685.7(s) 1683.7 (s) 1685.7(s) 1685.7(s) 1683.7(m) ---- 1712.8(s) 1712.8(s) 1712.8(s) 1712.8 (s) 1712.8(s) 1712.8(s) 1712.8(s) 1712.8(s) 1712.8(m) ---- Table 5. IR stretching frequencies of C=O (cm-1) in (x1) OCP and (1-x1) ketones systems. x1 0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 OCP+AC 1714.6(w) 1714.6(s) 1706.9(s) 1701.1(s) 1701.1(s) 1701.1(s) 1705.0(s) 1699.2(s) 1697.2(s) 1701.1(m) ---- O-H stretching vibrations: The non hydrogen-bonded hydroxyl group of phenol absorbs strongly in the 3584-3650 cm-1 region. The sharp free hydroxyl bands are observed in the vapour phase and in dilute solution in non polar solvent15. Intermolecular hydrogen bonding increases as the concentration of solution increases and additional bands appears at lower frequencies 3200-3500 cm-1. Hence in the present investigations (Table 6.0); phenolic O-H frequency OCP+AP 1683.7(s) 1679.9(s) 1679.9(s) 1678.0(s) 1676.0(s) 1674.1(s) 1672.2(s) 1670.0(s) 1668.3(s) 1668.3(s) ---- OCP+CYNO 1710.7(s) 1712.8(s) 1712.8(s) 1705.1(s) 1701.2(s) 1697.4(s) 1697.4(s) 1697.4(m) 1697.4(m) 1693.5(m) ---- decreases from x1 ≈ 0.1 - 0.6 and increases from x1 ≈ 0.7 - 0.9 for OCP + AC. This frequency increases from x1 ≈ 0.1 - 0.9 for OCP + AP (fig.7). The O-H frequency decreases from x1 ≈ 0.1 - 0.4 and increases from x1 ≈ 0.5 - 0.9 for OCP + CYNO. For OCP systems the sharp band is due to free -OH, while weak band is due to hydrogen bonded -OH. Two bands are observed in OCP + CYNO in x1 ≈ 0.6 0.9 and one sharp band is recorded for OCP + AC and OCP + AP over entire range of composition. Available online on www.ijprd.com 11 International Journal of Pharmaceutical Research & Development ISSN: 0974 – 9446 Table 6. IR stretching frequencies of O-H (cm-1) in (x1) OCP and (1-x1) ketones systems. OCP+AC OCP+AP OCP+CYNO x1 0 ---------0.1 3460.1(s) 3355.9(s) 3404.4(s) 3255.9(m) 0.2 3402.2(s) 3352.1(s) 3400.6 (s) 3255.9(s) 0.3 3442.7(s) 3354.0(s) 3277.1(s) 3265.5(s) 0.4 3400.3(s) 3392.8(s) 3265.5(s) 0.5 3394.5(s) 3398.3(s) 3369.7(s) 3294.5(s) 0.6 3386.8(s) 3404.1(s) 3369.7(s) 3302.2(m) 0.7 3444.6(s) 3409.9(s) 3400.6(s) 3381.3(s) 0.8 3454.3(s) 3425.3(s) 3524.0(m) 3431.4(s) 0.9 3427.3(s) 3438.8(s) 3524.0(s) 3448.84(m) 1.0 3456.2(s) 3456.2(s) 3456.2(s) The position and breadth of an -OH absorption band depends on the concentration of the solution. The more concentrated solution and the more -OH containing molecules form intermolecular hydrogen bonds. It is easier to stretch an O-H bond if it is hydrogen bonded, because the hydrogen is attached to oxygen of a neighboring molecule. Therefore, the stretch of a concentrated (hydrogen bonded) solution of OCP occurs at 3427.3 cm-1, whereas the stretch of a dilute solution (with little or no hydrogen bonding) occurs at 3460.1 cm-1 for OCP + AC system. However no such dilution effect is observed in other binary mixture. But other all systems show hydrogen bond effect at higher concentration Fig 5: (x1 ≈ 0.1 to 0.6) of OCP. It is seen that the O-H stretching frequency increases when mole fraction of OCP decreases. Higher values of O-H stretching frequency is observed at high mole fraction and lower values of O-H stretching frequency is recorded in between 0.2 to 0.5 mole fractions of OCP. This may be due to hydrogen bonding between phenolic O-H group and carbonyl group. The O-H stretching frequency of OCP is 3456.2 cm-1, which gets decrease in presence of ketone because of intermolecular hydrogen bonding between them. The binaries OCP + AP and OCP + CYNO show large decrease in the O-H stretching frequency. IR stretching frequencies of C = O (cm-1) for OCP + AP system. x1=0.1 x1=0.6 x1=0.2 x1=0.7 x1=0.3 x1=0.8 x1=0.4 x1=0.5 x1=0.9 Available online on www.ijprd.com 12 International Journal of Pharmaceutical Research & Development ISSN: 0974 – 9446 Fig 6: IR stretching frequencies of C = O (cm-1) for ODB + AP system. x1=0.1 x1=0.5 x1=0.2 x1=0.6 Spectrum of some OCP + ketones show two absorption bands -OH. The sharp band is due to free -OH while weak band is due to hydrogen bonded -OH. Presence of hydrogen bonding between -OH of OCP with oxygen of studied x1=0.3 x1=0.7 x1=0.8 x1=0.4 x1=0.9 ketones and absence of hydrogen bonding in systems of ODB + ketones is confirmed by FTIR. In case of ODB + Ketones, carbonyl stretching frequency is not so affected. Fig 7: IR stretching frequencies of O - H (cm-1) for OCP + AP system. x1=0.1 x1=0.6 x1=0.2 x1=0.7 The interesting behavior of intramolecular hydrogen bonds both from the practical and Available online on www.ijprd.com x1=0.3 x1=0.4 x1=0.8 x1=0.5 x1=0.9 theoretical points of view has received increased attention in recent years16-24. This can be attributed 13 International Journal of Pharmaceutical Research & Development to the fact that the value of hydrogen bond energy is only a few kilocalories per mole and can readily perturb by any change in its environment. This is especially important in studies of weekly bound complexes of ketones and OCP. ISSN: 0974 – 9446 9. Grunberg L, Trans. Faraday Soc., 1954, 50, 1293. 10. Nikam P S, Shewale R P, Borse R Y, Sawant A B & Hasan M, J Chem Eng Data., 2005, 50, 487. 11. Ravichandran G, Rao A S & Nambinarayanan T K, Indian J Pure Appl Phys. 1984, 32, 59. 12. Seales S and Tamres M, J Am Chem Soc., 1951, 73, 3704. 13. 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