Insight Into the Nature of Rim Bonds in Coronene
Document Type
Article
Journal/Book Title
The Journal of Physical Chemistry Part A: Molecules, Spectroscopy, Kinetics, Environment and General Theory
Publication Date
10-8-2018
Publisher
American Chemical Society
Award Number
NSF, Division of Chemistry (CHE) 1664379
Funder
NSF, Division of Chemistry (CHE) 1664379
Volume
122
Issue
43
First Page
8585
Last Page
8590
Abstract
Coronene is known in chemistry as an aromatic or even superaromatic molecule while it has 24 π-electrons which does not conform to the 4n + 2 Huckel’s rule. Chemical bonding description of it is not settled in chemistry and five models were reported in the literature. According to our model, coronene has two concentric π-systems responsible for aromaticity inside of the molecule. In addition to that there are six peripheral 2c–2e π-bonds, which makes coronene aliphatic/aromatic at the same time. However, recent experiments and calculations put in question the presence of peripheral π-bonds. In order to resolve this issue, we computationally studied reaction mechanism of the Cl2 molecule with C2H4, C6H6, and C24H12. As it turned out, coronene behaves in a way similar to ethylene by adding Cl2 molecule. Thus, it proves that coronene indeed has peripheral double bonds which is also consistent with its experimental geometrical features. Our chemical bonding model allows to identify the most reactive atoms in coronene and other PAHs; therefore, it is a matter of importance for combustion and soot formation studies.
Recommended Citation
Insight into The Nature of Rim Bonds in Coronene Nikita Fedik and Alexander I. Boldyrev The Journal of Physical Chemistry A 2018 122 (43), 8585-8590 DOI: 10.1021/acs.jpca.8b07937
