Solvent effects on tautomerism equilibria in heterocycles |
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| Authors: | F. J. Luque J. M. López-Bes J. Cemeli M. Aroztegui M. Orozco |
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| Affiliation: | (1) Departament de Farmàcia, Unitat Fisicoquímica, Facultat de Farmàcia, Universitat de Barcelona, Avgda. Diagonal s/n, E-08028 Barcelona, Spain, ES;(2) Departament de Bioquímica i Biologia Molecular, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1, E-08028 Barcelona, Spain, ES |
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| Abstract: | . High-level ab initio quantum mechanical methods have been used to analyze the tautomeric preferences in the gas phase and in aqueous solution of three important five-member heterocycles: 4-(5-)methylimidazole, 5-hydroxyisoxazole, and 3-hydroxypyrazole. Solvent effects have been introduced by means of self-consistent reaction field (SCRF) calculations at the ab initio level using our parametrized version of the polarizable continuum model developed by Miertus, Scrocco and Tomasi (MST), including geometry relaxation upon solvation. The extent to which the MST model, and SCRF methods in general, are suitable for the study of processes of this type is discussed. |
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| Keywords: | : Tautomeric equilibria Hetro-cycles Solvent effects Self-consistent reaction field Continuum electro statics |
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