环丁二烯真的因为反芳香性而高度不稳定吗？
Is cyclobutadiene really highly destabilized by antiaromaticity?
机构信息
Department of Chemistry, Center for Computational Quantum Chemistry, University of Georgia, Athens, GA 30602, USA.
出版信息
Chem Commun (Camb). 2012 Aug 28;48(67):8437-9. doi: 10.1039/c2cc33521b. Epub 2012 Jul 16.
PMID:22801355
Abstract
The high energy of cyclobutadiene (CBD) is not due primarily to "anti-aromaticity," but rather to angle strain, torsional strain, and Pauli repulsion between the parallel CC bonds. Estimations including block-localized wavefunction (BLW) computations conclude that the enormous ring strain (ca. 60 kcal mol(-1)) far exceeds its antiaromatic destabilization (only 16.5 kcal mol(-1)).
摘要
环丁二烯（CBD）的高能量并非主要归因于“反芳香性”，而是源于角张力、扭转应变以及平行 CC 键之间的 Pauli 斥力。包括块-localized 波函数 (BLW) 计算在内的估算表明，巨大的环应变（约 60 kcal mol(-1)) 远远超过其反芳香稳定性（仅 16.5 kcal mol(-1))。
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