Structural Chemistry

, Volume 22, Issue 2, pp 313–317 | Cite as

Solvent mediated reaction of 1-methyl-1H-tetrazoline-5-thione with iodine

  • Nataliya V. Aleshina
  • Margarita S. Chernov’yants
  • Igor N. Shcherbakov
  • Zoya A. Starikova
Original Research

Abstract

1-Methyl-1H-tetrazoline-5-thione (1) reacts with iodine in CHCl3 with formation of 1:1 stable σ-complex (logβ = 3.8 ± 0.1 is found by spectrophotometry). In the ethanol solution irreversible oxidation with formation of disulfide product 5,5′-dithiobis(1-methyl-1H-tetrazole) (2) is observed. The structure of (2) was determined by X-ray diffraction. Strong intermolecular interactions with shortened contacts are observed between sulfur atom of disulfide bridge and heterocyclic nitrogen of the neighboring molecule (S···N 3.0179(15) Å) forming infinite supramolecular chains which are further linked with π–π stacking interaction of tetrazole rings (interplane distance is 3.1685(6) Å).

Keywords

X-ray structure Heterocyclic compounds Stability constant Iodine chemistry 

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Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Nataliya V. Aleshina
    • 1
  • Margarita S. Chernov’yants
    • 2
  • Igor N. Shcherbakov
    • 2
  • Zoya A. Starikova
    • 3
  1. 1.Southern Scientific Center of Russian Academy of Sciences (SSC RAS)Rostov-on-DonRussian Federation
  2. 2.Southern Federal UniversityRostov-on-DonRussian Federation
  3. 3.A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of SciencesMoscowRussian Federation

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