Circuit resonance energy: A key quantity that links energetic and magnetic criteria of aromaticity

被引:140
|
作者
Aihara, J [1 ]
机构
[1] Shizuoka Univ, Fac Sci, Dept Chem, Oya, Shizuoka 4228529, Japan
关键词
D O I
10.1021/ja056430c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Energetic and magnetic criteria of aromaticity are different in nature and sometimes make different predictions as to the aromaticity of a polycyclic pi-system. Thus, some charged polycyclic g-systems are aromatic but paratropic. We derived the individual circuit contributions to aromaticity from the magnetic response of a polycyclic pi-system and named them circuit resonance energies (CREs). Each CRE has the same sign and essentially the same magnitude as the corresponding cyclic conjugation energy (CCE) defined by Bosanac and Gutman. Such CREs were found to play a crucial role in associating the energetic criteria for determining the degree of aromaticity with the magnetic ones. We can now interpret both energetic and magnetic criteria of aromaticity consistently in terms of CRIES. Ring-current diamagnetism proved to be the tendency of a cyclic pi-system to retain aromatic stabilization energy (ASE) at the level of individual circuits.
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页码:2873 / 2879
页数:7
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