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Chemical Bonding in Coronene, Isocoronene, and Circumcoronene
Author(s) -
Popov Ivan A.,
Boldyrev Alexander I.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200256
Subject(s) - coronene , delocalized electron , chemistry , ring (chemistry) , chemical physics , concentric , molecule , computational chemistry , density functional theory , molecular physics , organic chemistry , geometry , mathematics
Chemical‐bonding analysis in coronene, isocoronene, and circumcoronene has been performed by using the Adaptive Natural Density Partitioning (AdNDP) method. This analysis revealed that coronene and isocoronene have two globally delocalized concentric π‐systems. Circumcoronene does not have globally delocalized π‐systems; instead, it has seven local sextets and can be represented by a single Clar structure. Thus, today there are a few known polycyclic aromatic hydrocarbons with two concentric π‐systems, but there are as yet no examples of such molecules with three or more concentric π‐systems. The results revealed by the AdNDP analysis are consistent with the results obtained by the current‐density maps, NICS and NICS ZZ indices as well as MCI, PDI, I ring and δ indices.