A threshold for charge transfer in aromatic interactions?: A quantitative study of π-stacking interactions

被引：59

作者：

Gung, BW ^{[1
]}

Patel, M ^{[1
]}

Xue, XW ^{[1
]}

机构：

[1] Miami Univ, Dept Chem & Biochem, Oxford, OH 45056 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 25期

关键词：

D O I：

10.1021/jo051808a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Attractive interactions between substituted arenes in the parallel displaced configuration have been quantitatively studied using triptycene-derived molecular conformational reporters. Charge-transfer bands are observed for models where the interactions are between strong donor and acceptors. Substituent effects on the strength of the aromatic interaction follow opposite trends for strongly electron-deficient arenes and mildly perturbed arenes. The free energy of interactions for models with strong electron donors and acceptors does not follow a linear correlation in the Hammett plot. Electrostatic models alone do not account for the nonlinearity of the free energy-substituents plot.

引用

页码：10532 / 10537

页数：6

共 45 条

[1] MULTIPLE CHARGE TRANSFER BANDS IN COMPLEXES OF HEXAFLUOROBENZENE WITH AROMATIC AMINES [J].