QUANTUM-CHEMICAL STUDY OF THE REACTIVITY OF DI- AND TRINITROPYRAZOLES

Authors

  • И. Л. Далингер N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
  • Д. В. Хакимов N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
  • Т. К. Шкинева N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
  • И. А. Вацадзе N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
  • Г. П. Попова N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
  • Т. С. Пивина N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
  • С. А. Шевелев N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

DOI:

https://doi.org/10.1007/878

Keywords:

dinitropyrazoles, trinitropyrazoles, σ-complexes, nucleophilic substitution, quantum-chemical calculations, reactivity, selective substitution

Abstract

Quantum chemistry methods (DFT B3LYP/6-31G* (3-21G)) were used to calculate the three-dimensional and electronic structure of 4-chloro-3,5-dinitro- and 3,4,5-trinitropyrazoles, as well as their model σ-complexes. Possible reasons for the peculiar reactivity of 3,4,5-trinitropyrazole, 4‑chloro-3,5-dinitropyrazole, and their derivatives were examined.

Authors: I. L. Dalinger, D. V. Khakimov, T. K. Shkineva, I. A. Vatsadze, G. P. Popova, T. S. Pivina, and S. A. Shevelev

English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (11), pp 1646-1651

http://link.springer.com/article/10.1007/s10593-013-1187-3

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Published

2013-08-22

Issue

No. 11 (2012)

Section

Original Papers