On the aromatic stabilization of corannulene and coronene

Abstract

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.