Intra- and intermolecular N-H•••O hydrogen bonds in pyrrolyl derivatives of indane-1,3-dione - experimental and theoretical study

被引：32

作者：

Sigalov, M. ^{[1
]}

Shainyan, B. ^{[2
]}

Chipanina, N. ^{[2
]}

Ushakov, I. ^{[2
]}

Shulunova, A. ^{[2
]}

机构：

[1] Ben Gurion Univ Negev, Dept Chem, IL-84105 Beer Sheva, Israel

[2] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, Irkutsk 664033, Russia

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2009年 / 22卷 / 12期

关键词：

density functional theory; hydrogen bonds; IR; NMR spectroscopy; quantum chemical calculations; UV; NMR-SPECTROSCOPY; SPECTRA; C-13; 1,3-INDANDIONE; ANALOGS; SERIES; H...O; H-1;

D O I：

10.1002/poc.1573

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(Pyrrol-2-ylmethylene)-1,3-indandione (4) and 2-(pyrrol-2-ylmethylene)-3-dicyanomethylidene-1-indanone (5) were synthesized. Multinuclear and 2D-NMR, IR, UV spectroscopic investigations as well as quantum chemical calculations showed the presence of strong hydrogen bonding in these molecules. For both molecules, the presence of two conformers, with and without H-bond, was experimentally detected in the basic solvents (DMSO, acetone, pyridine) and the solvate complexes were theoretically calculated. Specific behavior of the intramolecular H-bonded complexes different from that of the intermolecular H-complexes is discussed. Copyright (C) 2009 John Wiley & Sons, Ltd.

引用

页码：1178 / 1187

页数：10

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