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

Abstract

1-Methyl-1H-tetrazoline-5-thione (1) reacts with iodine in CHCl 3 with formation of 1:1 stable r-complex (logb = 3.8 ± 0.1 is found by spectrophotometry). In the ethanol solution irreversible oxidation with formation of disulfide product 5,5 0 -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 (SÁÁÁN 3.0179(15) Å ) forming infinite supramolecular chains which are further linked with p-p stacking interaction of tetrazole rings (interplane distance is 3.1685(6) Å ).

Interplay of thermochemistry and Structural Chemistry, the Journal (volume 22, 2011, issues 1–3) and the discipline

“…In the experimental study by Aleshina et al [85], the reaction of 1-methyl-1H-tetrazoline-5-thione with elemental iodine in weakly polar aprotic chloroform and in dipolar amphiprotic ethanol was studied. While a 1:1 stable r-complex was formed in chloroform, 5,5 0 -dithiobis(1-methyl-1H-tetrazole) was obtained from ethanol due to a substantial charge transfer and initiates the formation of the disulfide oxidation product.…”