SPECTRAL AND QUANTUM-CHEMICAL STUDY OF NONEQUIVALENCE OF METHYLENE PROTONS IN 1,4-DIHYDROPYRIDINE DERIVATIVES

Authors

  • M. Петрова Latvian Institute of Organic Synthesis
  • Р. Мухамадеев Latvian Institute of Organic Synthesis
  • А. Чесноков Latvian Institute of Organic Synthesis
  • Б. Виганте Latvian Institute of Organic Synthesis
  • Б. Чекавичус Latvian Institute of Organic Synthesis
  • А. Плотниеце Latvian Institute of Organic Synthesis
  • Г. Дубурс Latvian Institute of Organic Synthesis
  • Э. Лиепиньш Latvian Institute of Organic Synthesis

DOI:

https://doi.org/10.1007/947

Keywords:

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

Abstract

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.

How to Cite
Petrova, M.; Muhamadejev, R.; Chesnokov, A.; Vigante, B.; Cekavicus, B.; Plotniece, A.; Duburs, G.; Liepinsh, E. Chem. Heterocycl. Compd. 2014, 49, 1631. [Khim. Geterotsikl. Soedin. 2013, 1760.]

For this article in the English edition see DOI 10.1007/s10593-014-1414-6

Author Biographies

M. Петрова, Latvian Institute of Organic Synthesis

Марина Петрова

Р. Мухамадеев, Latvian Institute of Organic Synthesis

Руслан Мухамадеев

А. Чесноков, Latvian Institute of Organic Synthesis

Андрей Чесноков

Б. Виганте, Latvian Institute of Organic Synthesis

Бригита Виганте

Б. Чекавичус, Latvian Institute of Organic Synthesis

Бригита Чекавичус

А. Плотниеце, Latvian Institute of Organic Synthesis

Айва Плотниеце

Г. Дубурс, Latvian Institute of Organic Synthesis

Гунарс Дубурс

Э. Лиепиньш, Latvian Institute of Organic Synthesis

Эдвардс Лиепиньш

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Published

2013-12-02

Issue

No. 11 (2013)

Section

Original Papers