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

doi:10.3390/molecules16098041

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

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

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

Latvian Institute of Organic Synthesis Aizkraukles 21 Street, Riga LV-1006, Latvia

* Author to whom correspondence should be addressed.

Received: 26 July 2011; in revised form: 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

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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.

AMA 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(9):8041-8052.

Chicago/Turabian Style

Petrova, Marina; Muhamadejev, Ruslan; Vigante, Brigita; Cekavicus, Brigita; Plotniece, Aiva; Duburs, Gunars; Liepinsh, Edvards. 2011. "Intramolecular C-H···O Hydrogen Bonding in 1,4-Dihydropyridine Derivatives." Molecules 16, no. 9: 8041-8052.

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