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Molecules 2011, 16(9), 8041-8052; doi:10.3390/molecules16098041

Intramolecular C-H···O Hydrogen Bonding in 1,4-Dihydropyridine Derivatives

Latvian Institute of Organic Synthesis Aizkraukles 21 Street, Riga LV-1006, Latvia
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Received: 26 July 2011 / Revised: 8 September 2011 / Accepted: 9 September 2011 / Published: 19 September 2011
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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; nucleophilic substitution; hydrogen bond; NMR spectra; quantum chemical calculations 1,4-dihydropyridines; bromination; nucleophilic substitution; hydrogen bond; NMR spectra; quantum chemical calculations
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Petrova, M.; Muhamadejev, R.; Vigante, B.; Cekavicus, B.; Plotniece, A.; Duburs, G.; Liepinsh, E. Intramolecular C-H···O Hydrogen Bonding in 1,4-Dihydropyridine Derivatives. Molecules 2011, 16, 8041-8052.

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