SPECIFIC C-H...N INTRAMOLECULAR INTERACTIONS IN THE VINYLOXY- AND VINYLTHIOPYRIDINE SERIES

Article abstract of DOI:10.1007/BF00472287

A weak hydrogen bond with the participation of the vinyl group α-hydrogen atom arises in 2-vinyloxypyridine and 2-vinylthiopyridine, which primarily exist in the s-trans-conformation, according to the 1H and 13C NMR data.This interaction does not take place in 2-vinyloxymethyl- and 2-vinyloxyethylpyridines, which primarily exist in the s-cis-conformation.The C-H...N intramolecular interaction also does not occur in o-vinyloxyaniline due to the specific features of the stereoelectronic state of the amino group nitrogen atom.