Abstract
1,3-Diphenyl-5-(2-benzothiazolyl)formazane exists in its crystalline state (based on x-ray crystal structure data) in the E 1,2 Z 2,3 Z 3,4-conformation, which is stabilized by intramolecular hydrogen bonding (IMHB); the proton is localized on the nitrogen atom which is bound to the heterocycle. In chloroform solutions 1(5)-aryl-3-phenyl-5(1)-(2-benzothiazolyl)formazanes exist in the form of equilibrium mixtures of their chelate and open E 1,2 Z 2,3 Z 3,4-forms, in which the first of these forms predominates. Based on their 13 C-NMR spectral data the tautomeric equilibrium involving these forms is shifted in favor of the benzothiazolylhydrazone form. The amount of tautomer containing the benzothiazolidene fragment structure increases in DMSO solution.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1268–1274, September, 1991.
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Shmelev, L.V., Kessenikh, A.V., Orlova, E.E. et al. Structure of 1(5)-aryl-3-phenyl-5(1)-(2-benzothiazolyl)formazanes. Chem Heterocycl Compd 27, 1023–1029 (1991). https://doi.org/10.1007/BF00484372
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DOI: https://doi.org/10.1007/BF00484372