STANDARD ENTHALPIES OF FORMATION IN THE GAS PHASE AND RELATIVE STABILITY OF TAUTOMERS OF C-NITRO-1,2,4-TRIAZOLE AND ISOMERS OF N-ALKYL-C-NITRO-1,2,4-TRIAZOLE: QUANTUM-CHEMICAL STUDIES

Authors

  • О. А. Ивашкевич Research Institute for Physico-Chemical Problems, Belarussian State University, Minsk 220030
  • Вадим Э. Матулис Research Institute for Physico-Chemical Problems, Belarussian State University, Minsk 220030
  • П. Д. Элькинд Research Institute for Physico-Chemical Problems, Belarussian State University, Minsk 220030
  • П. Н. Гапоник Research Institute for Physico-Chemical Problems, Belarussian State University, Minsk 220030
  • Г. Т. Суханов Institute of Problems of Chemical and Energetical Technologies, Siberian Branch of the Russian Academy of Sciences, Biisk 659322
  • А. Г. Суханова Institute of Problems of Chemical and Energetical Technologies, Siberian Branch of the Russian Academy of Sciences, Biisk 659322

DOI:

https://doi.org/10.1007/6893

Keywords:

C-nitro-1, 2, 4-triazole, isomerism, quantum-chemical calculations, B3YLP method, standard enthalpies of formation

Abstract

Quantum-chemical calculations of the standard enthalpies of formation in the gas phase of C-nitro-1,2,4-triazole and isomers of N-alkyl-C-nitro-1,2,4-triazoles  (Alk = Me, Et, i-Pr, t-Bu) were carried out by the B3LYP method using equations for the isodesmic reactions and isomerization reactions. The relative Gibbs free energies of tautomers and isomers in aqueous solution were calculated. For the tautomers of C-nitro-1,2,4-triazole the structural indexes of aromaticity were estimated and the electron population density of the Natural Bond Orbital was analyzed. The relative stabilities of the described tautomers and isomers in the gas phase and in solutions were discussed on the basis of the results of the calculations.

How to Cite
Ivashkevich, O. A.; Matulis, V. E.; Elkind, P. D.; Gaponik, P. N.;  Sukhanov, G. T.; Sukhanova, A. G.  Chem. Heterocycl. Compd. 2009, 45, 70. [Khim. Geterotsikl. Soedin. 2009, 83.]

For this article in the English edition see DOI 10.1007/s10593-009-0228-4

 

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Published

2022-07-12

Issue

No. 1 (2009)

Section

Original Papers