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

✍ Scribed by Andrei V. Afonin; Igor A. Ushakov; Svetlana Yu. Kuznetsova; Ol'ga V. Petrova; Elena Yu. Schmidt; Al'bina I. Mikhaleva

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
147 KB
Volume
40
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

^1^H and ^13^C 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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