Abstract
Mercaptoacetylhydrazones of aliphatic and aromatic aldehydes exist in the solutions as tautomeric mixtures of open-chain and cyclic 1,3,4-thiadiazine forms. The linear hydrazone form consists of a set of isomers due to the configurational and conformational isomerism. At growing bulk of the alkyl substituent at the C=N bond of the aliphatic aldehydes derivatives decreases the fraction of the cyclic tautomer; therewith the logarithms of the constants of the chain-ring tautomeric equilibrium correlate with the steric constants of the alkyl substituents. In the series of the aromatic aldehydes mercaptoacetylhydrazones the linear tautomer prevails, and the equilibrium position is insignificantlyt affected at variation of the electronic characteristics of the substituents in the aromatic ring.
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Original Russian Text © A.Yu.Ershov, I.V. Lagoda, S.I. Yakimovich, V,V. Pakal’nis, I.V. Zerova, A.V. Dobrodumov, V.V. Shamanina, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 5, pp. 678–684.
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Ershov, A.Y., Lagoda, I.V., Yakimovich, S.I. et al. Tautomerism and conformational isomerism of mercaptoacetylhydrazones of aliphatic and aromatic aldehydes. Russ J Org Chem 45, 660–666 (2009). https://doi.org/10.1134/S1070428009050030
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DOI: https://doi.org/10.1134/S1070428009050030