TAUTOMERIC AND CONFORMATIONAL ISOMERISM OF MERCAPTOACETYLHYDRAZONES OF METHYL ALKYL KETONES

Authors

  • A. Yu. Ershov Institute of High Molecular Compounds, Russian Academy of Sciences, St. Petersburg 199004
  • N. V. Koshmina Institute of High Molecular Compounds, Russian Academy of Sciences, St. Petersburg 199004

Keywords:

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

Abstract

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.

How to Cite
Ershov, A. Yu.; Koshmina, N. V. Chem. Heterocycl. Compd. 2004, 40, 926. [Khim. Geterotsikl. Soedin. 2004, 1076.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000044577.12949.9a

 

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Published

2004-07-25

Issue

No. 7 (2004)

Section

Original Papers