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Chemistry of Heterocyclic Compounds

, Volume 14, Issue 6, pp 617–622 | Cite as

Kinetic characteristics of the ring-chain tautomeric equilibria of 2,3,3-trimethyl-1-aryl-2-hydroxy-5-pyrrolidones

  • L. Yu. Yuzefovich
  • B. M. Sheiman
  • T. M. Filippova
  • V. G. Mairanovskii
Article

Abstract

The kinetics of the ring—chain tautomeric equilibria of a number of p-substituted 2,3,3-trimethyl-1-aryl-2-hydroxy-5-pyrrolidones in 50% aqueous pyridine were studied by dynamic PMR spectroscopy, and the effect of substituents on the kinetic parameters of this process was determined. The free energies of activation (ΔG≠) decrease regularly on passing from electron-donor to electron-acceptor substituents. A good correlation between ΔG≠ and the σ+ and σ substituent constants is observed. On the basis of the data obtained, it was concluded that the ratedetermining step in the process is detachment of a proton under the influence of the base to give the corresponding anion.

Keywords

Spectroscopy Free Energy Organic Chemistry Pyridine Kinetic Parameter 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1978

Authors and Affiliations

  • L. Yu. Yuzefovich
    • 1
  • B. M. Sheiman
    • 1
  • T. M. Filippova
    • 1
  • V. G. Mairanovskii
    • 1
  1. 1.All-Union Scientific-Research Vitamin InstituteMoscow

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