The infrared absorption spectra of 4-substituted-thiosemicarbazides, 5-(substituted)amino-1,2,3,4-thiatriazoles, and the corresponding isomeric tetrazolinethiones have been studied and structural assignments of importance to these systems made or suggested. Important conclusions drawn from the spectral data are: there is no suggestion of any thiol–thione tautomerism for the solid 4-substituted-thiosemicarbazides and that the thione structure predominates for these substances; that the so-called 5-thiol-tetrazoles also exist as thiones; and that the diazotization products of the 4-substituted-thiosemicarbazides yield 1,2,3,4,-thiatriazoles rather than the isomeric open chain thiocarbamyl azides. The C==S, —N—C==S, and cyclic —N—N==N— configurational assignments, which are of importance to the classes of compounds studied, are discussed.
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