Abstract
Ab initio calculations on the different associated structures of 2-pyrrolidinone with water and with itself were carried out using 3-21G and 6-31G* basis sets at the Hartree–Fock level, including electron correlation using second-order Møller–Plesset perturbation theory. The calculated free energy changes for the intermolecular hydrogen bonded dimer and hydrated species indicated that the molecular systems with cyclic dimerization and association with two water molecules are dominant. The results are compared to the available experimental data in the literature.
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Walmsley, J.A., Jacob, E.J. and Thompson, H.B., J. Phys. Chem., 80 (1976) 2745.
Walmsley, J.A., J. Phys. Chem., 82 (1978) 2031.
Jadzyn, J., Malecki, J. and Jadzyn, C., J. Phys. Chem., 82 (1978) 2128.
Hopman, R. and Bunsenges, B., Phys. Chem., 77 (1973) 52.
McDermott, D.P., J. Phys. Chem., 90 (1986) 2569.
De Smet, K., Kedziora, P., Jadzyn, J. and Hellemans, L., J. Phys. Chem., 100 (1996) 7662.
Pirila-Honkanen, P. and Ruostesuo, P., Thermochim. Acta, 156 (1989) 129.
Ruostesuo, P., Pirila-Honkanen, P. and Heikkinen, L., J. Phys. Org. Chem., 2 (1989) 565.
Al-Azzawi, S.F., Awwad, A.M., Al-Dujaili, A.H. and Al-Noori, M.K., J. Chem. Eng. Data, 35 (1990) 463.
Pirila-Honkanen, P., Physicochemical Properties of 2-Pyrrolidinone and N-Methylbenzenesulfonamide in Binary Solution Mixtures, Acta Univ. Oul. A284, Oulu University Press, Finland, 1996.
Pirila-Honkanen, P. and Ruostesuo, P., J. Chem. Eng. Data, 32 (1987) 303.
Ruostesuo, P. and Pirila-Honkanen, P., J. Sol. Chem., 19 (1990) 473.
Pirila-Honkanen, P., J. Sol. Chem., 24 (1995) 641.
Garcia, B., Hoyuelos, F.J., Alcalde, R. and Leal, J.M., Can. J. Chem., 74 (1996) 121.
Engberts, J.B.F.N., Perjessy, A., Blandamer, M.J. and Eaton, G., J. Chem. Soc., Faraday Trans., 88 (1992) 2493.
Malonowski, S., Bittrich, H.-J., Lempe, D., Reinhardt, K. and Wüstling, J.-U., Fluid Phase Equilibria, 98 (1994) 163.
Mehta, S.K., Chauan, R.K. and Triphati, A.D., J. Chem. Thermodyn., 29 (1997) 353.
Mehta, S.K., Chauan, R.K. and Dewan, R.K., J. Chem. Soc., Faraday Trans., 92 (1996) 1167.
Garcia, B., Herrea, C.A. and Leal, J.M., Thermochim. Acta, 180 (1991) 59.
Hehre, W.J., Radom, L., Schleyer, P.v.R. and Pople, J.A., Ab Initio Molecular Orbital Theory, Wiley, New York, NY, 1986.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Robb, M.A., Cheeseman, J.R., Keith, T.A., Petersson, G.A., Montgomery, J.A., Raghavachari, K., Al-Laham, M.A., Zakrzewski, V.G., Ortiz, J.V., Foresman, J.B., Cioslowski, J., Stefanov, B.B., Nanayakkara, A., Challacombe, M., Peng, C.Y., Ayala, P.Y. and Chen, W., GAUSSIAN94, Revision-B.3., Gaussian Inc., Pittsburgh, PA, 1995.
ChemOffice Pro for Windows, Cambridge Scientific Computing Inc., Cambridge, MA.
Warshel, A., Levitt, M. and Lifson, S., J. Mol. Spectrosc., 33 (1970) 84.
Treschanke, L. and Rademacher, P., J. Mol. Struct. (THEOCHEM), 122 (1985) 35.
Cosentino, U., Scolastica, C., Moro, G., Morosi, G. and Pitea, D., J. Mol. Struct. (THEOCHEM), 201 (1989) 199.
Riggs, N.V., Aust. J. Chem., 38 (1985) 1585.
Boeyens, J.C.A., Denner, L., Howard, A.S. and Michael, J.P., S. Afr. J. Chem., 39 (1986) 217.
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Yekeler, H., Guven, A. & Ozkan, R. Hydrogen bonding and dimeric self-association of 2-pyrrolidinone: An ab initio study. J Comput Aided Mol Des 13, 589–596 (1999). https://doi.org/10.1023/A:1008037504968
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DOI: https://doi.org/10.1023/A:1008037504968