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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors
  1. A. E. Obukhov
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  2. L. I. Belen'kii
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Additional information

Dedicated to Prof. A. Katritzky on his seventieth birthday.

Russian International Friendship University, 117302 Moscow. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, 117913 Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1181–1194, September, 1998.

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Obukhov, A.E., Belen'kii, L.I. Localization of electronic excitation and change in the direction of electrophilic substitution reactions in some phenylazoles, 2-furylazoles, and 2-thienylazole. Chem Heterocycl Compd 34, 1011–1022 (1998). https://doi.org/10.1007/BF02251544

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  • DOI: https://doi.org/10.1007/BF02251544

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