Steric Crowding Can Stabilize a Labile Molecule: Solving the Hexaphenylethane Riddle

被引：207

作者：

Grimme, Stefan ^{[1
]}

Schreiner, Peter R. ^{[2
]}

机构：

[1] Univ Bonn, Inst Phys & Theoret Chem, Mulliken Ctr Theoret Chem, D-53115 Bonn, Germany

[2] Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 52期

关键词：

density functional theory; dispersion energy; steric interactions; thermochemistry; van der Waals forces; DENSITY-FUNCTIONAL THEORY; TRIVALENT CARBON; ENERGY; BOND; ISOMERS; BENZENE; LENGTH; DIMER; SETS;

D O I：

10.1002/anie.201103615

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

12 not so angry men: Hexaphenylethane is unstable, a phenomenon traditionally attributed to steric repulsion between the six phenyl rings. However, adding 12 bulky tert-butyl groups, one to each of the 12 meta positions, gives a stabile ethane derivative (see space-filling model and potential energy curve for the dissociation of the central C-C bond). This unexpected stabilization is shown to result from attractive dispersion interactions between the substituents. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：12639 / 12642

页数：4

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