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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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Molecules 2011, 16(9), 8041-8052; https://doi.org/10.3390/molecules16098041
Received: 26 July 2011 / Revised: 8 September 2011 / Accepted: 9 September 2011 / Published: 19 September 2011
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. View Full-Text
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
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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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