Chemistry of Heterocyclic Compounds

, Volume 22, Issue 6, pp 633–639 | Cite as

Tautomerism of azine derivatives. 11.14N-NMR and17O-NMR investigation of intrachelate tautomerism of acylmethylpyridines

  • V. V. Lapachev
  • S. A. Stekhova
  • I. Ya. Mainagashev
  • M. A. Fedotov
  • V. E. Khall
  • V. P. Mamaev


Intrachelate [1, 5]-sigmatropic tautomerism in a series of acylmethylpyridines has been studied by14N- and17O-NMR spectroscopy. Principles of tautomer modelling or simulation have been proposed and examined, nitrogen and oxygen chemical shift spectra have been determined, and the accuracy of this method for the determination of tautomer composition has been evaluated. The presence of acceptor (electron withdrawing) substituents in the acylmethyl side-chain fragment has been found to stabilize the NH-tautomer.


Oxygen Nitrogen Spectroscopy Organic Chemistry Chemical Shift 
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Copyright information

© Plenum Publishing Corporation 1986

Authors and Affiliations

  • V. V. Lapachev
    • 1
  • S. A. Stekhova
    • 1
  • I. Ya. Mainagashev
    • 1
  • M. A. Fedotov
    • 1
  • V. E. Khall
    • 1
  • V. P. Mamaev
    • 1
  1. 1.Institute of Organic Chemistry, Siberian BranchAcademy of Sciences of the USSRNovosibirsk

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