title: 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).
authors.affiliation: Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland. miked@chem.uw.edu.pl
authors.forename: Michał A
authors.initials: MA
authors.lastname: Dobrowolski
authors.forename: Arkadiusz
authors.initials: A
authors.lastname: Ciesielski
authors.forename: Michał K
authors.initials: MK
authors.lastname: Cyrański
mesh_terms: D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D011084:Polycyclic Aromatic Hydrocarbons; D011083:Polycyclic Compounds; C434863:corannulene; C012256:coronene