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

Molecules. 2011 Sep 19;16(9):8041-52. doi: 10.3390/molecules16098041.

Authors

Marina Petrova¹, Ruslan Muhamadejev, Brigita Vigante, Brigita Cekavicus, Aiva Plotniece, Gunars Duburs, Edvards Liepinsh

Affiliation

¹ Latvian Institute of Organic Synthesis Aizkraukles 21 Street, Riga LV-1006, Latvia. marina@osi.lv

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Dihydropyridines / chemical synthesis
Dihydropyridines / chemistry*
Hydrogen Bonding
Magnetic Resonance Spectroscopy
Molecular Conformation
Structure-Activity Relationship

Substances

Dihydropyridines
1,4-dihydropyridine