Open AccessAromaticity Evaluations of Planar [6]Radialenes
Author(s) -
Guillaume Berionni,
Judy I. Wu,
Paul von Ragué Schleyer
Publication year - 2014
Publication title -
organic letters
Language(s) - Uncategorized
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol5029699
Subject(s) - aromaticity , coronene , chemistry , triphenylene , benzene , character (mathematics) , planar , computational chemistry , harmonic oscillator , annulene , chemical shift , resonance (particle physics) , molecule , atomic physics , organic chemistry , physics , quantum mechanics , geometry , mathematics , computer graphics (images) , computer science
The aromatic character of fused polycyclic systems varies with the nature of their annulated rings. Computed extra cyclic resonance energies (ECREs) reveal that the central six membered rings (6MRs) of the heterocyclic fused congeners 1-5 are "[6]radialene-like", but that the central 6MRs of triphenylene 9, coronene 10, and isocoronene 11 are "benzene-like." Comparisons with geometric (harmonic oscillator model of aromaticity, HOMA) and magnetic (nucleus independent chemical shifts, NICS) criteria illustrate the multifaceted nature of aromaticity in 1-11.