Chemistry of Heterocyclic Compounds

, Volume 40, Issue 7, pp 926–930 | Cite as

Tautomeric and Conformational Isomerism of Mercaptoacetylhydrazones of Methyl Alkyl Ketones

  • A. Yu. Ershov
  • N. V. Koshmina


Mercaptoacetylhydrazones of methyl alkyl ketones (Alk = Me, Et, Pr, i-Pr, i-Bu, s-Bu, t-Bu) exist in solutions as a tautomeric mixture of linear and cyclic 1,3,4-thiadiazine forms.The linear hydrazone form exists as a set of conformers caused by restricted rotation of the amide group relative to the C–N bond. It is shown that tautomeric equilibrium constants correlate with the steric constants of the alkyl substituents, ES.

mercaptoacetylhydrazones 1,3,4-thiadiazin-5(4H)-ones ring-chain tautomerism the Taft equation 


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© Plenum Publishing Corporation 2004

Authors and Affiliations

  • A. Yu. Ershov
  • N. V. Koshmina

There are no affiliations available

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