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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 ??-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).

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Dobrowolski, M. A.; Ciesielski, A.; Cyranski, M. K. Phys. Chem. Chem. Phys., 2011, 13, 20557-20563 (Paywall)Contributed by Steven Bachrach.Reposted from Computational Organic Chemistry with permissionHow should one assess the aromatic stabilization...