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Chemistry of Heterocyclic Compounds

, Volume 46, Issue 9, pp 1133–1137 | Cite as

Ring-chain tautomerism of 2-mercaptobenzoylhydrazones of aromatic aldehydes

  • B. V. Chernitsa
  • A. Yu. ErshovEmail author
  • V. A. Doroshenko
  • S. I. Yakimovich
  • I. V. Lagoda
  • I. V. Zerova
  • V. V. Pakal’nis
  • V. V. Shamanin
Article
  • 121 Downloads

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.

Keywords

benzo-1,3,4-thiadiazepines 2-mercaptobenzoylhydrazones ring-chain tautomerism Hammett equation 

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Copyright information

© Springer Science+Business Media, Inc. 2010

Authors and Affiliations

  • B. V. Chernitsa
    • 1
  • A. Yu. Ershov
    • 1
    Email author
  • V. A. Doroshenko
    • 1
  • S. I. Yakimovich
    • 2
  • I. V. Lagoda
    • 3
  • I. V. Zerova
    • 2
  • V. V. Pakal’nis
    • 2
  • V. V. Shamanin
    • 1
  1. 1.Institute of Macromolecular CompoundsRussian Academy of SciencesSaint-PetersburgRussia
  2. 2.Saint-Petersburg State UniversitySaint-PetersburgRussia
  3. 3.Scientific Research Test Center (Medical and Biological Defence), Federal Research Test Institute of Military MedicineDefence Ministry of Russian FederationSaint-PetersburgRussia

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