Hydrogen bonding isosteres:: Bimolecular carboxylic acid and amine-N-oxide interactions mediated via CH•••O hydrogen bonds

被引：25

作者：

Baures, PW ^{[1
]}

Wiznycia, A ^{[1
]}

Beatty, AM ^{[1
]}

机构：

[1] Kansas State Univ, Dept Chem, Manhattan, KS 66506 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2000年 / 8卷 / 07期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0968-0896(00)00090-0

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The X-ray structures of cocrystals between 2,2'-dipyridyl-N,N'-dioxide (1) with fumaric acid (2), itaconic acid (3), succinic acid (4), and oxalic acid (5) were solved to determine if concurrent CH ... O interactions were capable of orienting the bimolecular association of the two molecules. Cocrystals 1.2, 1.3 and 1.4 produce cyclic hydrogen bonded motifs employing pair-wise OH ... O and CH ... O hydrogen bonds, whereas cocrystal 1.5 forms analogous OH ... O hydrogen bonds with a different set of intermolecular CH ... O hydrogen bonds. Evidence of cocrystal formation was also observed for these complexes by differential scanning calorimetry and FT-IR spectroscopy. The structures of 1.2, 1.3 and 1.4 demonstrate the potential of the pair-wise OH ... O and CH ... O hydrogen bonding interactions and serve to illustrate their use as hydrogen bonding isosteres in crystal engineering, molecular recognition, and drug design. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1599 / 1605

页数：7

共 47 条

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