Prediction of the acidities of organic bases in aqueous solution using AM1 COSMO solvation model

Guven A., Yekeler H., Ozkan R.

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, vol.499, pp.13-19, 2000 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 499
  • Publication Date: 2000
  • Doi Number: 10.1016/s0166-1280(99)00271-7
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.13-19
  • Keywords: pyrazole, tautomeric equilibrium, acidity, basicity, proton affinity, molecular properties/structures, molecular orbital, GAS-PHASE ACIDITIES, TAUTOMERIC EQUILIBRIA, AB-INITIO, ALCOHOLS, 3-HYDROXYPYRAZOLE
  • Anadolu University Affiliated: No


Potentially tautomeric pyrazole-3-ones were studied, in order to predict their tautomeric equilibrium constants and pK(a) values, using the semiempirical AM1 COSMO solvation model at the SCF level in aqueous solution. Syn and anti conformers of the hydroxy form were also investigated to find a more stable form. The oxo forms have been found to be more stable than the hydroxy ones. The results obtained from the tautomeric equilibria and acidity calculations are in good agreement with experimental data. (C) 2000 Elsevier Science B.V. All rights reserved.