C—H···X (X = N, O, S) intramolecular interaction in 1-vinyl-2-(2'-heteroaryl)pyrroles as monitored by 1H and 13C NMR spectroscopy

Autor: Afonin, Andrei V., Ushakov, Igor A., Kuznetsova, Svetlana Yu., Petrova, Ol'ga V., Schmidt, Elena Yu., Mikhaleva, Al'bina I.
Zdroj: Magnetic Resonance in Chemistry; February 2002, Vol. 40 Issue: 2 p114-122, 9p
Abstrakt: 1H and 13C NMR spectroscopy of a series of 1-vinyl-2-(2'-heteroaryl)-pyrroles were employed for the analysis of their electronic and spatial structure. The C—H···N intramolecular interaction between the α-hydrogen of the vinyl group and the pyridine nitrogen, a kind of hydrogen bonding, was detected in 1-vinyl-2-(2'-pyridyl)pyrrole, which disappeared in its iodide methyl derivative. It was shown that this interaction is stronger than the C—H···O and C—H···S interactions in 1-vinyl-2-(2'-furyl)- and -2-(2'-thienyl)-pyrroles. Copyright © 2001 John Wiley & Sons, Ltd.
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