Organic fluorine hardly ever accepts hydrogen bonds

被引：903

作者：

Dunitz, JD ^{[1
]}

Taylor, R ^{[1
]}

机构：

[1] CAMBRIDGE CRYSTALLOG DATA CTR,CAMBRIDGE CB2 1EZ,ENGLAND

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 1997年 / 3卷 / 01期

关键词：

ab initio calculations; Cambridge Structural Database; fluorine compounds; hydrogen bonds; protein data bank; X-RAY-DIFFRACTION; CRYSTAL-STRUCTURE; INTERMOLECULAR INTERACTIONS; PERTURBATION-THEORY; MOLECULAR-STRUCTURE; CARBOXYLIC-ACIDS; COMPLEXES; DERIVATIVES; ELASTASE; BINDING;

D O I：

10.1002/chem.19970030115

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Statistical analysis of structural data and detailed inspection of individual crystal structures culled from the Cambridge Structural Database and the Brookhaven Protein Data Bank show that covalently bound fluorine (in contrast to anionic fluoride) hardly ever acts as a hydrogen-bond acceptor. The weakness of covalently bound fluorine as hydrogen-bond acceptor is backed by results of new molecular orbital calculations on model systems using ab initio intermolecular perturbation theory (IMPT), and is in accord with results of other physicochemical studies and with the physical properties of fluorinated organic compounds. Factors influencing the strength of hydrogen bonding in extended systems are discussed.

引用

页码：89 / 98

页数：10

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