Localization of electronic excitation and change in the direction of electrophilic substitution reactions in some phenylazoles, 2-furylazoles, and 2-thienylazole

Authors

  • А. E. Обухов Russian International Friendship University, 117302 Moscow
  • Л. И. Беленький N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, 117913 Moscow

Abstract

NMR, IR, UV, and fluorescence spectral data and semiempirical quantum chemical PPP and INDO/S methods were used to refine the electronic structure of several azoles and analyze the change in course of electrophilic aromatic substitution reactions involving addition and dissociation in going from free bases to protonated forms. The electronically excited singlet and triplet states of the protonated forms of the mono- and bicyclic systems studied feature excitation localization different from the free molecules. The results of quantum chemical modelling of the change in the reactivities of these systems are given.

How to Cite
Obukhov, A. E.; Belen'kii, L. I. Chem. Heterocycl. Compd. 1998, 34, 1011. [Khim. Geterotsikl. Soedin. 1998, 34, 1181.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02251544

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Published

1998-09-25

Issue

No. 9 (1998)

Section

Original Papers