平面[6]轮烯的芳香性评估。

Aromaticity evaluations of planar [6]radialenes.

作者信息

Berionni Guillaume, Wu Judy I-Chia, Schleyer Paul V R

机构信息

†Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 München, Germany.

‡Department of Chemistry, Center for Computational Quantum Chemistry, University of Georgia, Athens, Georgia 30602, United States.

出版信息

Org Lett. 2014 Dec 5;16(23):6116-9. doi: 10.1021/ol5029699. Epub 2014 Nov 19.

DOI:10.1021/ol5029699

PMID:25409485

Abstract

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.

摘要

稠合多环体系的芳香性随其稠合环的性质而变化。计算得到的额外环外共振能（ECREs）表明，杂环稠合同系物1 - 5的中心六元环（6MRs）呈“[6] - 类环戊二烯”结构，但三亚苯9、晕苯10和异晕苯11的中心6MRs呈“苯类”结构。与几何标准（芳香性的谐振子模型，HOMA）和磁性标准（核独立化学位移，NICS）的比较说明了1 - 11中芳香性的多面性。