σ-antiaromaticity in cyclobutane, cubane, and other molecules with saturated four-membered rings

被引：96
|
作者：
Moran, D
Manoharan, M
Heine, T
Schleyer, PV
机构：
[1] Univ Georgia, Athens, GA 30602 USA
[2] Univ Erlangen Nurnberg, Inst Organ Chem, Computat Chem Ctr, D-91054 Erlangen, Germany
[3] Tech Univ Dresden, Inst Phys Chem, D-01062 Dresden, Germany
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 01期
关键词：
D O I：
10.1021/ol027159w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Dissected nucleus-independent chemical shift (NICS) analyses of cycloalkanes and cage hydrocarbons reveal contrasting ring current effects, diatropic in three- and five-membered and paratropic in four-membered ring systems. The large shielding effects of the C-C bonds of the archetypal or-aromatic, cyclopropane, are magnified in tetrahedrane and related structures. The remarkable deshielding effect of the cyclobutane C-C(sigma) bonds is general: cubane and cages with four-membered rings are strongly deshielding (i.e., sigma-antiaromatic).
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页码：23 / 26
页数：4
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