It has been shown by 1H NMR spectroscopy that 2-mercaptobenzoylhydrazones of aromatic aldehydes 2-HSC6H4CONHN=CHC6H4X (X = 4-NO2, 3-NO2, 4-Br, H, 4-Me, 4-MeO, 4-Me2N) exist in DMSO-d6 solution as tautomeric mixtures of linear and cyclic benzo-1,3,4-thiadiazepine forms. The linear hydrazone form is represented by (E,Z′)-conformational isomers, differing in the disposition relative to the amide C–N bond. It was shown that the logarithm of the tautomeric equilibrium constant K T correlates with the σ-constants of the substituents in the aromatic nucleus.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1404–1409, September, 2010.
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Chernitsa, B.V., Ershov, A.Y., Doroshenko, V.A. et al. Ring-chain tautomerism of 2-mercaptobenzoylhydrazones of aromatic aldehydes. Chem Heterocycl Comp 46, 1133–1137 (2010). https://doi.org/10.1007/s10593-010-0638-3
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DOI: https://doi.org/10.1007/s10593-010-0638-3