How aromatic are large (4n+2)π annulenes?

被引：99
|
作者：
Wannere, CS [1 ]
Schleyer, PV [1 ]
机构：
[1] Univ Georgia, Dept Chem, Computat Chem Anex, Athens, GA 30602 USA
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 06期
关键词：
D O I：
10.1021/ol027571b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Graphics While the total aromatic stabilization energies (ASE) of the [n]annulenes, from C6H6 to C66H66, converge to ca. 22 kcal/mol, the ASEs per pi-electron decrease markedly. Bond length alternation (which depends on the theoretical level) only reduces stabilization somewhat but influences the magnetic properties (NICS, proton chemical shifts, and magnetic susceptibilities) considerably. Nevertheless, these magnetic criteria, when based on the most realistic structures, agree that the aromaticities of the larger annulenes decrease and then nearly vanish.
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页码：865 / 868
页数：4
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