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Updated: May 29, 2026
09:35
Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
On the aromatic stabilization of corannulene and coronene
Michał A Dobrowolski1, Arkadiusz Ciesielski, Michał K Cyrański
1Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland. miked@chem.uw.edu.pl
Physical Chemistry Chemical Physics : PCCP
|September 17, 2011
Summary
This study estimates the aromatic stabilization energy (ASE) for corannulene and coronene using homodesmotic reactions. Planar corannulene exhibits greater stabilization than its bowl-shaped form, with coronene showing higher overall ASE.
Area of Science:
- Computational chemistry
- Organic chemistry
- Physical chemistry
Background:
- Aromatic stabilization energy (ASE) is a key metric for understanding the stability of polycyclic aromatic hydrocarbons (PAHs).
- Corannulene and coronene are significant PAHs with unique structural and electronic properties.
Purpose of the Study:
- To accurately estimate the aromatic stabilization energy (ASE) of corannulene and coronene.
- To compare the ASE of planar versus bowl-shaped corannulene.
- To investigate the impact of substituents on ASE.
Main Methods:
- Utilized a set of homodesmotic reactions to calculate ASE.
- Employed polycyclic reference structures to account for strain effects in corannulene.
- Applied reactions to balance syn/anti mismatches in substituted derivatives.
Main Results:
- Estimated ASE for corannulene at 44.5 kcal mol⁻¹.
- Found planar corannulene to be more stabilized by cyclic π-electron delocalization (10.7 kcal mol⁻¹) than the bowl-shaped isomer.
- Calculated ASE for coronene to be 58.4 kcal mol⁻¹.
Conclusions:
- Homodesmotic reactions provide a reliable method for determining ASE in complex PAHs.
- Structural conformation significantly influences the aromatic stabilization of corannulene.
- Coronene exhibits a higher aromatic stabilization energy compared to corannulene.
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