Direct assessment of sigma-aromaticity in three-membered rings by perturbation theory

被引：4

作者：

Furusaki, A

机构：

[1] Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060, Kita-ku

来源：

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 1996年 / 362卷 / 03期

关键词：

sigma-aromaticity; perturbation theory; three-membered ring;

D O I：

10.1016/0166-1280(95)04415-9

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The existence of sigma-aromaticity in three-membered rings has been examined by applying perturbation theory to localized-bond models based on orthogonal hybrid AOs from STO-3G and 3-21G MO calculations. The STO-3G and 3-21G sigma-aromatic energies of cyclopropane are estimated to be 323 and 330 kJ mol(-1), respectively. It is shown that the sigma-aromaticity is caused mainly by the three-orbital-six-electron interaction among the three bonds forming the ring, and further that the stabilization due to this interaction originates in the great stability of the lowest a(1)' MO of the ring system.

引用

页码：365 / 377

页数：13

共 23 条

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[2]

BINKLEY JS, 1980, GAUSSIAN 80

[3]

COULSON CA, 1949, PHILOS MAG, V40, P1

[4] STRAIN IN NON-TETRAHEDRAL CARBON ATOMS [J].