Solvent mediated reaction of 1-methyl-1H-tetrazoline-5-thione with iodine
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- Aleshina, N.V., Chernov’yants, M.S., Shcherbakov, I.N. et al. Struct Chem (2011) 22: 313. doi:10.1007/s11224-010-9710-y
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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).