Molecular torsion balances: Evidence for favorable orthogonal dipolar interactions between organic fluorine and amide groups

被引：102

作者：

Fischer, Felix R. ^{[1
]}

Schweizer, W. Bernd ^{[1
]}

Diederich, Francois ^{[1
]}

机构：

[1] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 43期

关键词：

amides; dipolar interactions; fluorine; mutant cycles; torsion balance;

D O I：

10.1002/anie.200702497

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Figure Presented) Finding the right balance: An indole-extended molecular torsion balance has the geometry for measuring a truly orthogonal noncovalent interaction between a C-F bond dipole and an amide carbonyl group (see picture, green F, red O, blue N). Employing a double-mutant cycle approach, negative interaction free enthalpies were determined. Thus orthogonal dipolar interactions can be a new tool for stabilizing protein-ligand complexes and assembling supramolecular architectures. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：8270 / 8273

页数：4

共 15 条

[1] Chemical double-mutant cycles for the measurement of weak intermolecular interactions: Edge-to-face aromatic interactions [J].