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

被引：32
作者：
Afonin, AV
Ushakov, IA
Kuznetsova, SY
Petrova, OV
Schmidt, EY
Mikhaleva, AI
机构：
[1] Inst Chem, Irkutsk 664033, Russia
[2] Irkutsk Tech Univ, Irkutsk 664074, Russia
来源：
MAGNETIC RESONANCE IN CHEMISTRY | 2002年 / 40卷 / 02期
关键词：
NMR; H-1; C-13; 1-vinyl-2-(2 '-heteroaryl)-pyrroles; C-H center dot center dot center dot X (X = N; O; S) intramolecular interaction;
D O I：
10.1002/mrc.969
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
H-1 and C-13 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-(HN)-N-... intramolecular interaction between the a-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-(HO)-O-... and C-(HS)-S-... interactions in 1-vinyl-2-(2'-furyl)- and -2-(2'-thienyl)-pyrroles. Copyright (C) 2001 John Wiley Sons, Ltd.
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收藏
页码：114 / 122
页数：9
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