Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland.
Phys Chem Chem Phys. 2011 Dec 14;13(46):20557-63. doi: 10.1039/c1cp21994d. Epub 2011 Sep 15.
The application of set of homodesmotic reactions allowed us to estimate the aromatic stabilization energy (ASE) of corannulene and coronene. Appropriate reactions have been applied to balance syn/anti mismatches in di-, tetra- and hexamethylene substituted derivatives. Based on many different polycyclic reference structures that compensate the effect of strain in the corannulene moiety the value of ASE comes to 44.5 kcal mol(-1). Planar corannulene is more stabilized by cyclic π-electron delocalization by ca. 10.7 kcal mol(-1), as compared with a bowl-shaped system. A similar approach for coronene leads to an ASE equal to 58.4 kcal mol(-1).
套 Homodesmotic 反应的应用使我们能够估计并五苯和蔻烯的芳构化稳定能（ASE）。适当的反应已被应用于平衡二烯、四烯和六亚甲基取代衍生物中的顺/反错配。基于许多不同的多环参考结构，这些结构补偿了并五苯部分的应变效应，ASE 的值为 44.5 kcal mol(-1)。与碗状体系相比，平面并五苯通过环状π电子离域更稳定，约为 10.7 kcal mol(-1)。对于蔻烯，类似的方法导致 ASE 等于 58.4 kcal mol(-1)。
