Improved Resonance Energies of Nonalternant Hydrocarbons. An ω-Technique Approach
Improved Resonance Energies of Nonalternant Hydrocarbons. An ω-Technique Approach
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改进非交替碳氢化合物的共振能量。
DOI：
10.1246/bcsj.53.2689
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发表时间：
1980
期刊：
影响因子：
--
通讯作者：
J. Aihara
中科院分区：
文献类型：
--
作者：
J. Aihara
将Wheland和Mann的ω-技巧引入芳香性图论中，以提高非交替烃的共振能。对于这些化合物，ω-技术共振能或多或少小于基于最简单的Huckel分子轨道模型计算的共振能。特别是，迄今为止被认为是芳香族的几种化合物被预测为基本上是烯属的，具有大大降低的共振能。它们是calicene、sesquifulvalene、azulene、dibenzo[cd，gh]pentalene和cyclohepta[def]fluorene。它们的化学性质的许多方面显然与改进的共振能量相一致。讨论了用亲电取代作为芳香性判据的可能局限性。交替碳氢化合物的共振能不因ω-技术的应用而改变。
The ω-technique of Wheland and Mann was introduced into the graph theory of aromaticity in order to improve the resonance energies of nonalternant hydrocarbons. For these compounds, the ω-technique resonance energy was more or less smaller than the resonance energy calculated on the basis of the simplest Huckel MO model. Especially, several compounds thus far considered to be aromatic were predicted to be substantially olefinic with much reduced resonance energies. They are calicene, sesquifulvalene, azulene, dibenzo[cd,gh]pentalene, and cyclohepta[def]fluorene. Many aspects of their chemistry were evidently consonant with the improved resonance energies. Possible limitation of the use of electrophilic substitution as a criterion of aromaticity was discussed. Resonance energies of alternant hydrocarbons are not modified by application of the ω-technique.