Aromaticity Evaluations of Planar [6]Radialenes

被引：19

作者：

Berionni, Guillaume ^{[1
]}

Wu, Judy I-Chia ^{[2
]}

Schleyer, Paul V. R. ^{[2
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

[2] Univ Georgia, Dept Chem, Ctr Computat Quantum Chem, Athens, GA 30602 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 23期

关键词：

INDEPENDENT CHEMICAL-SHIFTS; INDUCED BOND LOCALIZATION; ELECTRON DELOCALIZATION; GEOMETRIC CONTRIBUTIONS; MOLECULAR-STRUCTURE; CORONENE; STABILIZATION; RINGS; SEPARATION; COMPLEXES;

D O I：

10.1021/ol5029699

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：6116 / 6119

页数：4

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