Russian Chemical Bulletin

, Volume 47, Issue 2, pp 327–331 | Cite as

Synthesis and molecular structure of 5-(1-aminoisoindolenin-3-ylidene-amino)-1,3,4-thiadiazole-2(3H)-thione

  • O. V. Shishkin
  • E. V. Kudrik
  • M. K. Islyaikin
  • A. V. Lyubimtsev
  • S. A. Siling
Organic Chemistry
Received:
Revised:

Abstract

The structure of 5-(1-aminoisoindolenin-3-ylideneamino)-1,3,4-thiadiazole-2(3H)-thione was studied by X-ray diffraction analysis and UV and IR spectroscopy. In the crystal, the molecule of the title compound is planar in spite of the substantially shortened intramolecular N…S contact. The factors that determine the structure of the heterocycle, namely, the nature of the N…S interaction, conjugation effects, and the tautomerism, were analyzed based on quantum-chemical calculations performed by the AM1 method.

Key words

1,3,4-thiadiazole-2(3H)-thione isoindolenine crystal solvate molecular structure X-ray diffraction analysis 
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Copyright information

© Plenum Publishing Corporation 1998

Authors and Affiliations

  • O. V. Shishkin
    • 1
  • E. V. Kudrik
    • 2
  • M. K. Islyaikin
    • 2
  • A. V. Lyubimtsev
    • 2
  • S. A. Siling
    • 1
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation
  2. 2.Ivanovo State Academy of Chemistry and TechnologyIvanovoRussian Federation

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