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Density, Refractive Index, Speed of Sound and Computational Studies of Intermolecular Interactions in Binary Mixtures of 2-Chloroaniline with Butanols (1-Butanol, 2-Butanol) at T = (303.15–318.15) K

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Abstract

Densities (ρ), refractive indices (n D) and speeds of sound (u) were measured for the binary mixtures of 2-chloroaniline with butanols (1-butanol, 2-butanol) over the entire range of mole fraction at 303.15, 308.15, 313.15 and 318.15 K under atmospheric pressure. From the experimental data, the values of molar volume (V m), isentropic compressibility (k S ), intermolecular free length (L f), specific acoustic impedance (Z), molar refraction (R m), atomic polarization (P a), polarizability (α), deviation in molar volume (ΔV m), deviation in isentropic compressibility (Δk s ), deviation in intermolecular free length (ΔL f) and deviation in refractive index (Δn D) have been calculated and fitted with Redlich–Kister type polynomial equations by the method of least-squares. The experimental reduced Redlich–Kister deviation properties were also determined, and the results reveal formation of hydrogen bonds between 2-chloroaniline and the butanol mixtures. The formation of hydrogen bonds in the binary mixture systems was further confirmed by FT-IR spectra. The optimized geometry, harmonic vibrational wave numbers and bond characteristics, of pure and equimolar hydrogen bonded complexes, have been calculated theoretically from the ab-intio Hartree–Fock (HF) and density functional theory (DFT-B3LYP) methods with 6-31 + G and 6-311 + G basis sets using Gaussian 09 software.

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References

  1. Todres, Z.V.: Effects of Hydrogen Bonding. Organic Chemistry in Confining Media, pp. 89–102. Springer International Publishing, Berlin (2013)

    Book  Google Scholar 

  2. Zaitseva, K.V., Varfolomeev, M.A., Novikov, V.B., Solomonov, B.N.: Enthalpy of cooperative hydrogen bonding in complexes of tertiary amines with aliphatic alcohols: calorimetric study. J. Chem. Thermodyn. 43, 1083–1090 (2011)

    Article  CAS  Google Scholar 

  3. Vijaya Krishna, T., Madhu Mohan, T.: Study of molecular interactions in the polar binary mixtures of N-methyl aniline and alcohols using excess dielectric and thermodynamic parameters. J. Chem. Thermodyn. 47, 267–275 (2012)

    Article  CAS  Google Scholar 

  4. Bricknell, B.C.: Experimental and Theoretical Studies of Hydrogen Bonding. University of Natal, Durban (1995)

    Google Scholar 

  5. Joshi, S.S., Aminabhavi, T.M.: Excess Volumes of binary mixtures of anisole with bromobenzene, o-dichloro-benzene, o-chloroaniline and p-dioxane at 298.15, 303.15, 308.15 and 313.15 K. Fluid Phase Equilib. 60, 319–326 (1990)

    Article  CAS  Google Scholar 

  6. Jeevanandham, P., Kumar, S., Periyasamy, P.: Densities, viscosities, refractive indices and excess properties of ortho-and meta-chloroaniline with 2-alkoxyethanols at 303.15 K. J. Mol. Liq. 188, 203–209 (2013)

    Article  CAS  Google Scholar 

  7. Pandiyan, V., Oswal, S.L., Malek, N.I., Vasantharani, P.: Thermodynamic and acoustic properties of binary mixtures of ethers. V. Diisopropyl ether or oxolane with 2-or 3-chloroanilines at 303.15, 313.15 and 323.15 K. Thermochim. Acta 524, 140–150 (2011)

    CAS  Google Scholar 

  8. Nain, A.K.: Densities and volumetric properties of binary mixtures of formamide with 1-butanol, 2-butanol, 1,3-butanediol and 1,4-butanediol at temperatures between 293.15 and 318.15 K. J. Solution Chem. 36, 497–516 (2007)

    Article  CAS  Google Scholar 

  9. Spasojevic, V.D., Djordjevic, B.D., Serbanovic, S.P., Radovic, I.R., Kijevcanin, M.L.: Densities, refractive indices, viscosities, and spectroscopic study of 1-amino-2-propanol + 1-butanol and + 2-butanol solutions at (288.15 to 333.15) K. J. Chem. Eng. Data 59, 1817–1829 (2014)

    Article  CAS  Google Scholar 

  10. Nain, A.K., Srivastava, T., Pandey, J.D., Gopal, S.: Densities, ultrasonic speeds and excess properties of binary mixtures of methyl acrylate with 1-butanol, or 2-butanol, or 2-methyl-1-propanol, or 2-methyl-2-propanol at temperatures from 288.15 to 318.15 K. J. Mol. Liq. 149, 9–17 (2009)

    Article  CAS  Google Scholar 

  11. Becke, A.D.: Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648–5652 (1993)

    Article  CAS  Google Scholar 

  12. Lee, C., Yang, W., Parr, R.G.: Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37, 785–789 (1988)

    Article  CAS  Google Scholar 

  13. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li., X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, Toyota, M. K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E.K. Kudin, N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J. W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman J.B., Ortiz, J.V., Cioslowski, J., Fox, D.J.: Gaussian 09, Revision A.02. Gaussian, Inc., Wallingford, CT (2009)

  14. Redlich, O., Kister, A.T.: Algebraic representation of thermodynamic properties and the classification of solutions. J. Ind. Eng. Chem. 40, 345–348 (1948)

    Article  Google Scholar 

  15. Dean, J.A.: Lange’s Handbook of Chemistry. McGraw-Hill, New York (1956)

    Google Scholar 

  16. Desnoyers, J.E., Perron, G.: Treatment of excess thermodynamic quantities for liquid mixtures. J. Solution Chem. 26, 749–755 (1997)

    Article  CAS  Google Scholar 

  17. Das, D., Ouerfelli, N.: The relative reduced Redlich-Kister and Herráez equations for correlating excess properties of N,N-dimethylacetamide + formamide binary mixtures at temperatures from 298.15 K to 318.15 K. J. Solution Chem. 41, 1334–1351 (2012)

    Article  CAS  Google Scholar 

  18. Ramana, G.V., Raj Gopal, E., Murthy, N.M.: Ultrasonic studies on dilute solutions of water in n-alcohols and 2-alkoxyethanol. Indian J. Pure Appl. Phys. 43, 259–264 (2005)

    CAS  Google Scholar 

  19. Glinski, J.: Additivity of sound velocity in binary liquid mixtures. J. Solution Chem. 31, 59–70 (2002)

    Article  CAS  Google Scholar 

  20. Beatriz, G., Villares, A., Lopez, M.C., Royo, F.M., Lafuente, C.: Refractive indices and molar refractions for isomeric chlorobutanes with isomeric butanols. Phys. Chem. Liquids 43, 13–23 (2005)

    Article  Google Scholar 

  21. Thirumaran, S., George, D.: Ultrasonic study of intermolecular association through hydrogen bonding in ternary liquid mixtures. ARPN J. Eng. Appl. Sci. 4, 1–11 (2009)

  22. Rama Rao, G.V., Sarma, V.A., Rambabu, C.: Excess volumes, deviation in viscosities and compressibilities of binary mixtures consisting of morpholine, piperidine with methanol and pyridine at different temperatures. Indian J. Pure Appl. Phys. 42, 820–826 (2004)

    Google Scholar 

  23. Kannappan, V., Jaya Santhi, R.: Ultrasonic investigation of induced dipole-induced dipole interactions in binary liquid mixtures at 298 K. Indian J. Pure Appl. Phys. 44, 815–819 (2006)

    CAS  Google Scholar 

  24. Thirumaran, S., Murugan, R., Prakash, N.: Acoustic study of intermolecular interactions in binary liquid mixtures. J. Chem. Pharm. Res. 2, 53–61 (2010)

  25. Wypych, G.: Handbook of Solvents. Chem Tec Publishing, Ontario (2001)

    Google Scholar 

  26. Nikam, P.S., Kharat, S.J.: Excess molar volumes and deviations in viscosity of binary mixtures of N,N-dimethylformamide with aniline and benzonitrile at (298.15, 303.15, 308.15, and 313.15) K. J. Chem. Eng. Data 48, 972–976 (2003)

    Article  CAS  Google Scholar 

  27. Fort, R.J., Moore, W.R.: Adiabatic compressibilities of binary liquid mixtures. Trans. Faraday Soc. 61, 2102–2111 (1965)

    Article  CAS  Google Scholar 

  28. Oswal, S.L., Patel, N.B.: Speed of sound, isentropic compressibility, viscosity, and excess volume of binary mixtures. 2. Alkanenitriles + dimethylformamide, + dimethylacetamide, and + dimethyl sulfoxide. J. Chem. Eng. Data 45, 225–230 (2000)

    Article  CAS  Google Scholar 

  29. Karthika, M., Senthilkumar, L., Kanakaraju, R.: Theoretical studies on hydrogen bonding in caffeine–theophylline complexes. Comp. Theoretical Chem. 979, 54–63 (2012)

    Article  CAS  Google Scholar 

  30. Silverstein, R.M., Bassler, G.C., Morrik, T.C.: Spectroscopic Identification of Organic Compounds, 5th edn. Wiley, Singapore (1991)

    Google Scholar 

  31. Pathak, S., Kumar, A., Tandon, P.: Molecular structure and vibrational spectroscopic investigation of 4-chloro-4′dimethylamino-benzylidene aniline using density functional theory. J. Mol. Struc. 981, 1–9 (2010)

    Article  CAS  Google Scholar 

  32. Mohan, T.M., Sastry, S.S., Murthy, V.R.K.: Conformational and dielectric relaxation studies on hydrogen bonded binary mixture of isopropyl alcohol in methyl benzoate and ethyl benzoate. J. Mol. Struc. 973, 157–162 (2010)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors are thankful to the Managements of Vignan Institute of Technology & Science, Hyderabad, and Vasireddy Venkatadri Institute of Technology, Guntur, for their encouragement towards the present research work. One of the authors (M. Chandra Sekhar) is thankful to Dr. M. Venkataramana, Principal, Vignan Institute of Technology & Science, Deshmukhi, for his moral support in all aspects of the research work. They are also thankful to Dr. R. L. Gardas, Department of Chemistry, Indian Institute of Technology, Chennai, for his valuable suggestions and moral support in all aspects of the research work.

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Authors and Affiliations

  1. Department of Physics, Vignan Institute of Technology and Science, Deshmukhi, Telangana, India

    M. Chandra Sekhar

  2. Department of Physics, Vasireddy Venkatadri Institute of Technology, Nambur, Andhra Pradesh, India

    T. Madhu Mohan & T. Vijaya Krishna

  3. Department of Physics, Government First Grade College, Hosakote, Bangalore Rural, Karnataka, India

    A. Venkatesulu

  4. Department of Chemistry, S.V. Arts Degree & P.G. College (T.T.D’S), Tirupati, Andhra Pradesh, India

    K. Siva Kumar

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  1. M. Chandra Sekhar
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  2. T. Madhu Mohan
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  3. T. Vijaya Krishna
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  4. A. Venkatesulu
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Correspondence to T. Madhu Mohan.

Appendix

Appendix

Experimental values of the densities, speeds of sound and refractive indices (Table 7).

Table 7 Density (ρ), refractive index (n D) and speed of sound (u) values for system 1 and system 2 at temperatures from 303.15 to 318.15 K and atmospheric pressure
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Chandra Sekhar, M., Madhu Mohan, T., Vijaya Krishna, T. et al. Density, Refractive Index, Speed of Sound and Computational Studies of Intermolecular Interactions in Binary Mixtures of 2-Chloroaniline with Butanols (1-Butanol, 2-Butanol) at T = (303.15–318.15) K. J Solution Chem 44, 237–263 (2015). https://doi.org/10.1007/s10953-015-0306-4

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