This article is cited in 35 papers

Some new views on the tautomerisation mechanism

J. A. Kereselidze, T. Sh. Zarqua, T. J. Kikalishvili, E. J. Churgulia, M. S. Makaridze

Tbilisi Ivane Javakhishvili State University, Department of Chemistry

Abstract: Published data on the prototropic tautomerism of some carbonyl and nitrogen-containing acyclic and heterocyclic compounds are systematised. Mechanisms of intramolecular and intermolecular proton transfer in tautomerisation reactions are considered. On the basis of the results of semiempirical and ab initio quantum-chemical calculations, preference is given to an intermolecular collective (dimeric, trimeric, tetrameric or oligomeric) mechanism. A new approach to the description of the solvent effect on the prototropic tautomeric equilibrium is proposed. The bibliography includes 107 references.

Received: 22.04.2002

DOI: 10.1070/RC2002v071n12ABEH000727

 English version: Russian Chemical Reviews, 2002, 71:12, 993–1003

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