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Teoret. i eksperim. khimiya. 2004. Vol.40 No. 2. p. 75-82

Quantum-Chemical Study of Intermediates Formed
in Addition Reaction of Phenylsulphenium Cation to Substituted Acetylenes


A. M. Nesterenko, V. I. Staninets

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

The reaction pathways for interaction of substituted acetylenes (X-C≡C-Y, X, Y-H, Me, Ph, CN) with phenylsulphenium cation were studied by quantum-chemical methods. It is shown that the reactions pro- ceed via acyclic and cyclic species. The inductive and polarizing role of the substituents in acetylenes is the factor which determins the properties and structure of intermediates, and electron donating properties of the substituents are of less value. The resonance effect of phenyl substituent plays leveling role on charge distribution.

Key words phenylsulphenium cation, substituted acetylenes, intermediates, configuration, electron structure, relative
stability, ab initio calculation.