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Teoret. i eksperim. khimiya. 2004. Vol.40 No. 4. p. 204-208

Quantum-Chemical Analysis of Routes for Ring Transformation
of 2-Phenacyl-1H-benzimidazole Phenylhydrazone


A. M. Nesterenko, A. Ya. Ilchenko, I. B. Dzvinchuk, M. O. Lozinskii

Institute of Organic Chemistry, National Academy of Sciences of Ukraine
5 Murmanska Vul., 02094 Kyiv, Ukraine. E-mail: iochkiev@ukrpack.net

Quantum-chemical calculations for ring transformation of 2-phenacyl-1H-benzimidazole phenylhydrazone into pyrazole compound are consistent with experimental data. The transformation is impossible at heating and acid catalysis, but it is real under conditions of acylation reaction. It proceeds via selective formation and spontaneous intramolecular reconstruction of the corresponding N-acylbenzimidazolium salt.

Key words Acylation, benzimidazoles, hydrazones, PM3 procedure, STO-3G procedure, reaction mechanisms, pyra-
zoles, ring transformation.