Homoheteroaromaticity: the case study of azepine and dibenzazepine

被引：26

作者：

Dardonville, C ^{[1
]}

Jimeno, ML ^{[1
]}

Alkorta, I ^{[1
]}

Elguero, J ^{[1
]}

机构：

[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2004年 / 2卷 / 11期

关键词：

D O I：

10.1039/b314742h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Geometrical and energetic DFT calculations as well as GIAO and NICS chemical shifts have been calculated for 1H-azepine and 5H-dibenz[b,f]azepine and their cations. The last compound has been studied experimentally by H-1 and C-13 NMR in neutral and acidic conditions establishing that the cation corresponds to an N-protonated structure. The conclusion is that the neutral molecules are antiaromatic while the cations are aromatic (homoheteroaromaticity).

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页码：1587 / 1591

页数：5

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