Investigation of C-H•••X (X = N, O, S) intramolecular hydrogen bond in 1-vinyl-2-(2′-heteroaryl)pyrroles by ab initio calculations

被引：21

作者：

Afonin, AV ^{[1
]}

Toryashinova, DSD ^{[1
]}

Schmidt, EY ^{[1
]}

机构：

[1] Inst Chem, Chem Phys Lab, Irkutsk 664033, Russia

来源：

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 2004年 / 680卷 / 1-3期

关键词：

ab initio; intramolecular hydrogen bonding C-H...X; chemical shifts;

D O I：

10.1016/j.theochem.2004.02.020

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The C-(HX)-X-... (X = N, O, S) intramolecular hydrogen bond between the alpha-hydrogen of the vinyl group and the corresponding heteroatom in the series of 1-vinyl-2-(2'-heteroaryl)pyrroles was examined by ab initio calculations at the B3LYP/6-311(d,p) level. It was shown that the C-H... N hydrogen bond is stronger than the C-(HO)-O-... hydrogen bond and the latter is, in turn, stronger than the C-(HS)-S-... hydrogen bond. This conclusion is supported by calculations of H-1 NMR chemical shieldings. (C) 2004 Elsevier B.V. All rights reserved.

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页码：127 / 135

页数：9

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