Chemistry of Heterocyclic Compounds

, Volume 49, Issue 11, pp 1631–1639 | Cite as

Spectral and Quantum-Chemical Study of Nonequivalence of Methylene Protons in 1,4-Dihydropyridine Derivatives*

  • M. PetrovaEmail author
  • R. Muhamadejev
  • A. Chesnokov
  • B. Vigante
  • B. Cekavicus
  • A. Plotniece
  • G. Duburs
  • E. Liepinsh

Structural characteristics of 1,4-dihydropyridines influencing the nonequivalence of the diastereotopic methylene protons in substituents at positions 2 and 6 were studied. The combined effect of magnetically anisotropic groups and intramolecular hydrogen bonds leads to a considerable difference in the chemical shifts of the methylene protons of the AB system. The unusual reversible temperature evolution of these proton signals in monocyclic 1,4-dihydropyridines is associated with two simultaneous conformational processes. It was estimated that the energetically most favorable conformations are stabilized by an intramolecular СН⋯О hydrogen bond.


1,4-dihydropyridines 1Н NMR spectroscopy hydrogen bond nonequivalence of methylene protons quantum-chemical calculations 


This project was supported by the Latvian National Research Program “Biomedicine”.


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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • M. Petrova
    • 1
    Email author
  • R. Muhamadejev
    • 1
  • A. Chesnokov
    • 1
  • B. Vigante
    • 1
  • B. Cekavicus
    • 1
  • A. Plotniece
    • 1
  • G. Duburs
    • 1
  • E. Liepinsh
    • 1
  1. 1.Latvian Institute of Organic SynthesisRigaLatvia

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