Abstract
According to data from the1H and13C NMR spectra in nonpolar media and the mass spectra, alkylidene derivatives of thiobenzhydrazide have a 1,3,4-thiadiazol-2-ine structure rather than a thiobenzhydrazone structure. The products of condensation of thiobenzhydrazide with acetone and anisaldehyde in methanol undergo partial isomerization to thiobenzhydrazones. The hydrochlorides of the compounds under discussion are the corresponding 1,3,4-thiadiazolinium salts, in which the proton is coordinated with the N4, atom. The 2-phenyl-5,5-dimethyl-1,3,4-thiadiazol-2-ine anion has a noncyclic thioenolate structure.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 904–910, July, 1982.
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Zelenin, K.N., Khrustalev, V.A., Alekseev, V.V. et al. 2-phenyl-1,3,4-thiadiazol-2-ines. Chem Heterocycl Compd 18, 683–689 (1982). https://doi.org/10.1007/BF00568942
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DOI: https://doi.org/10.1007/BF00568942