A theoretical study of annular tautomerism of pyrrolotetrazoles in the gas phase View Full Text


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Article Info

DATE

2015-03

AUTHORS

Vadim Yu. Zubarev, Rostislav E. Trifonov, Vladimir A. Ostrovskii, Dietrich Moderhack

ABSTRACT

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. On the contrary, for pyrrolotetrazoles with electron-withdrawing substituents (CN or Cl), the most stable form is the 1Н-tautomer, where the pyrrole fragment is aromatic. This effect may be determined by the differences of the relative electron accepting of the heterocyclic half-rings. More... »

PAGES

246-249

References to SciGraph publications

  • 1983-08. Tetrazole derivatives. 28. σ constants of 5-tetrazolyl groups in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 1985-07. Heteroaromaticity (review) in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • Identifiers

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    http://scigraph.springernature.com/pub.10.1007/s10593-015-1692-7

    DOI

    http://dx.doi.org/10.1007/s10593-015-1692-7

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