A THEORETICAL STUDY OF ANNULAR TAUTOMERISM OF PYRROLOTETRAZOLES IN THE GAS PHASE

Авторы

  • Vadim Yu. Zubarev Saint Petersburg State Technological Institute (Technical University)
  • Rostislav E. Trifonov Saint-Petersburg State University, Institute of Chemistry, 26 Universitetskii pr., Peterhof, Saint-Petersburg, 198504, Russia
  • Vladimir A. Ostrovskii СПбГТИ
  • Dietrich Moderhack Institute of Medicinal and Pharmaceutical Chemistry, Technical University, Beethovenstrasse 55, Braunschweig, D-38106, Germany

DOI:

https://doi.org/10.1007/2225

Ключевые слова:

pyrrolotetrazoles, aromaticity, HF and DFT calculations, tautomerism, total energies

Аннотация

The structure and tautomerism of pyrrolotetrazoles have been studied with quantum-chemical methods (HF/6-31G** and DFT B3LYP/ANO-S) in the gas phase. According to the calculations of the total energies of various prototropic forms of these heterocyclic systems (1Н-, 3Н-, 5Н- and 7Н-tautomers), it was shown that for unsubstituted pyrrolotetrazole and its derivatives containing methyl substituents at the carbon atom(s), the most stable form is the 5Н-tautomer where aromaticity of the tetrazole fragment is maintained. With electron-withdrawing substituents (CN or Cl) the most stable form is the 1Н-tautomer where, on the contrary, the pyrrole fragment is aromatic. This effect may be determined by the differences of the relative electronegativity of the heterocyclic half-rings.

How to Cite
Zubarev, V. Yu.; Trifonov, R. E.; Ostrovskii, V. A.; Moderhack, D. Chem. Heterocycl. Compd. 2015, 51, 246. [Khim. Geterotsikl. Soedin. 2015, 51, 246.]

For this article in the English edition see DOI 10.1007/s10593-015-1692-7

Биография автора

Vladimir A. Ostrovskii, СПбГТИ

д.х.н., Кафедра химии и технологии органических соединений азота

Загрузки

Опубликован

2015-02-25

Выпуск

Том 51 № 3 (2015)

Раздел

Оригинальные статьи