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https://doi.org/10.1007/s10593-008-0052-2

has been cited by the following article:

• TITLE: Ring-Chain Tautomerism of the Condensation Products of 2-Mercaptobenzohydrazide with Aliphatic and Aromatic Aldehydes: Influence of Electronic and Steric Factors

  AUTHORS: Andrei Yu Ershov, Igor V. Lagoda, Marina Yu Vasileva, Stanislav I. Yakimovich, Boris V. Chernitsa, Lyudmila Yu Kuleshova, Lyudmila V. Pavlova, Aleksandr V. Yakimansky

  KEYWORDS: Hammett and Taft Equations, Ring-Chain Tautomerism 2-Mercaptobenzoylhydrazones, Benzo-1, 3, 4-Thiadiazepines

  JOURNAL NAME: Open Access Library Journal, Vol.4 No.5, May 12, 2017

  ABSTRACT: It has been shown by 1H and 13C NMR spectroscopy that 2-mercaptobenzoyl-hydrazones of aliphatic and aromatic aldehydes exist in solution as tautomeric mixtures of linear and cyclic benzo-1,3,4-thiadiazepine forms. The linear hydrazone form is represented by (E,E')-and (E,Z')-conformational isomers, differing in the disposition relative to the amide C–N bond. 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 ES steric constants of the alkyl substituents. In the series of the aromatic aldehydes 2-mercaptobenzoylhydrazones the linear tautomer prevails, and the logarithms of the tautomeric equilibrium constants KT correlate with the σ-constants of the substituents in the aromatic nucleus.