Stacked-Ring Aromaticity: An Orbital Model

被引：49

作者：

Bean, D. E. ^{[1
]}

Fowler, P. W. ^{[1
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 24期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1021/ol802417n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Visualization of induced current density using the ipsocentric CHF/CTOCD-DZ/6-31G** approach gives a direct demonstration of the literature proposal of reversal of [4n]annulene antiaromaticity on stacking cyclooctatetraene (COT) rings into a superphane. Through-space interactions lead to a closed-shell in which paratropicity of planar COT units is quenched, and layered diatropic currents arise from magnetic response of two pairs of frontier orbitals. A general orbital model rationalizes the differences in current between stacked aromatic and antiaromatic rings.

引用

页码：5573 / 5576

页数：4

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