Intramolecular C-H⋯O hydrogen bonding in 1,4-dihydropyridine derivatives

Marina Petrova; Ruslan Muhamadejev; Brigita Vigante; Brigita Cekavicus; Aiva Plotniece; Gunars Duburs; Edvards Liepinsh

doi:10.3390/molecules16098041

Intramolecular C-H⋯O hydrogen bonding in 1,4-dihydropyridine derivatives

Marina Petrova, Ruslan Muhamadejev, Brigita Vigante, Brigita Cekavicus, Aiva Plotniece, Gunars Duburs, Edvards Liepinsh

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

27 Citations (Scopus)

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Abstract

The diastereotopy of the methylene protons at positions 2 and 6 in 1,4-dihydropiridine derivatives with various substituents has been investigated. NMR spectroscopy and quantum chemistry calculations show that the CH⋯O intramolecular hydrogen bond is one of the factors amplifying the chemical shift differences in the 1H-NMR spectra.

Original language	English
Pages (from-to)	8041-8052
Number of pages	12
Journal	Molecules
Volume	16
Issue number	9
DOIs	https://doi.org/10.3390/molecules16098041
Publication status	Published - Sept 2011
Externally published	Yes

Keywords*

1,4-dihydropyridines
Bromination
Hydrogen bond
NMR spectra
Nucleophilic substitution
Quantum chemical calculations

Field of Science*

1.4 Chemical sciences
1.6 Biological sciences
3.1 Basic medicine

Publication Type*

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

Access to Document

10.3390/molecules16098041Licence: CC BY-NC-SA

Intramolecular C-H···O Hydrogen BondingFinal published version, 562 KBLicence: CC BY-NC-SA

Cite this

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abstract = "The diastereotopy of the methylene protons at positions 2 and 6 in 1,4-dihydropiridine derivatives with various substituents has been investigated. NMR spectroscopy and quantum chemistry calculations show that the CH⋯O intramolecular hydrogen bond is one of the factors amplifying the chemical shift differences in the 1H-NMR spectra.",

keywords = "1,4-dihydropyridines, Bromination, Hydrogen bond, NMR spectra, Nucleophilic substitution, Quantum chemical calculations",

author = "Marina Petrova and Ruslan Muhamadejev and Brigita Vigante and Brigita Cekavicus and Aiva Plotniece and Gunars Duburs and Edvards Liepinsh",

year = "2011",

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language = "English",

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T1 - Intramolecular C-H⋯O hydrogen bonding in 1,4-dihydropyridine derivatives

AU - Petrova, Marina

AU - Muhamadejev, Ruslan

AU - Vigante, Brigita

AU - Cekavicus, Brigita

AU - Plotniece, Aiva

AU - Duburs, Gunars

AU - Liepinsh, Edvards

PY - 2011/9

Y1 - 2011/9

N2 - The diastereotopy of the methylene protons at positions 2 and 6 in 1,4-dihydropiridine derivatives with various substituents has been investigated. NMR spectroscopy and quantum chemistry calculations show that the CH⋯O intramolecular hydrogen bond is one of the factors amplifying the chemical shift differences in the 1H-NMR spectra.

AB - The diastereotopy of the methylene protons at positions 2 and 6 in 1,4-dihydropiridine derivatives with various substituents has been investigated. NMR spectroscopy and quantum chemistry calculations show that the CH⋯O intramolecular hydrogen bond is one of the factors amplifying the chemical shift differences in the 1H-NMR spectra.

KW - 1,4-dihydropyridines

KW - Bromination

KW - Hydrogen bond

KW - NMR spectra

KW - Nucleophilic substitution

KW - Quantum chemical calculations

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U2 - 10.3390/molecules16098041

DO - 10.3390/molecules16098041

M3 - Article

C2 - 21931285

AN - SCOPUS:80053248957

SN - 1420-3049

VL - 16

SP - 8041

EP - 8052

JO - Molecules

JF - Molecules

IS - 9

ER -

Intramolecular C-H⋯O hydrogen bonding in 1,4-dihydropyridine derivatives

Abstract

Keywords*

Field of Science*

Publication Type*

Access to Document

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