Spectral and quantum-chemical study of nonequivalence of methylene protons in 1,4-dihydropyridine derivatives

M. Petrova; R. Muhamadejev; A. Chesnokov; B. Vigante; B. Cekavicus; A. Plotniece; G. Duburs; E. Liepinsh

doi:10.1007/s10593-014-1414-6

Spectral and quantum-chemical study of nonequivalence of methylene protons in 1,4-dihydropyridine derivatives

M. Petrova, R. Muhamadejev, A. Chesnokov, B. Vigante, B. Cekavicus, A. Plotniece, G. Duburs, E. Liepinsh

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

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 CH...O hydrogen bond.

Original language	English
Pages (from-to)	1631-1639
Number of pages	9
Journal	Chemistry of Heterocyclic Compounds
Volume	49
Issue number	11
DOIs	https://doi.org/10.1007/s10593-014-1414-6
Publication status	Published - Feb 2014
Externally published	Yes

Keywords*

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

Field of Science*

1.4 Chemical sciences

Publication Type*

1.1. Scientific article indexed in Web of Science and/or Scopus database

Access to Document

10.1007/s10593-014-1414-6

Cite this

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title = "Spectral and quantum-chemical study of nonequivalence of methylene protons in 1,4-dihydropyridine derivatives",

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 CH...O hydrogen bond.",

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

author = "M. Petrova and R. Muhamadejev and A. Chesnokov and B. Vigante and B. Cekavicus and A. Plotniece and G. Duburs and E. Liepinsh",

note = "Funding Information: This project was supported by the Latvian National Research Program {"}Biomedicine{"}.",

year = "2014",

month = feb,

doi = "10.1007/s10593-014-1414-6",

language = "English",

volume = "49",

pages = "1631--1639",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer New York",

number = "11",

}

TY - JOUR

T1 - Spectral and quantum-chemical study of nonequivalence of methylene protons in 1,4-dihydropyridine derivatives

AU - Petrova, M.

AU - Muhamadejev, R.

AU - Chesnokov, A.

AU - Vigante, B.

AU - Cekavicus, B.

AU - Plotniece, A.

AU - Duburs, G.

AU - Liepinsh, E.

N1 - Funding Information: This project was supported by the Latvian National Research Program "Biomedicine".

PY - 2014/2

Y1 - 2014/2

N2 - 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 CH...O hydrogen bond.

AB - 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 CH...O hydrogen bond.

KW - 1,4-dihydropyridines

KW - NMR spectroscopy

KW - hydrogen bond

KW - nonequivalence of methylene protons

KW - quantum-chemical calculations

UR - http://www.scopus.com/inward/record.url?scp=84893799382&partnerID=8YFLogxK

U2 - 10.1007/s10593-014-1414-6

DO - 10.1007/s10593-014-1414-6

M3 - Article

AN - SCOPUS:84893799382

SN - 0009-3122

VL - 49

SP - 1631

EP - 1639

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

IS - 11

ER -

Spectral and quantum-chemical study of nonequivalence of methylene protons in 1,4-dihydropyridine derivatives

Abstract

Keywords*

Field of Science*

Publication Type*

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