Issue 11, 2004
From the journal:

Organic & Biomolecular Chemistry

Homoheteroaromaticity: the case study of azepine and dibenzazepine†

Christophe Dardonville,*a   María Luisa Jimeno,a   Ibon Alkortaa  and  José Elgueroa  

* Corresponding authors

a Instituto de Química Médica, CSIC, Juan de la Cierva 3, E-28006 Madrid, Spain

Abstract

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 1H and 13C 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).

Graphical abstract: Homoheteroaromaticity: the case study of azepine and dibenzazepine

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Article information

DOI
https://doi.org/10.1039/B314742H
Article type
Paper
Submitted
17 Nov 2003
Accepted
26 Mar 2004
First published
11 May 2004

Org. Biomol. Chem., 2004,2, 1587-1591

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Homoheteroaromaticity: the case study of azepine and dibenzazepine

C. Dardonville, M. L. Jimeno, I. Alkorta and J. Elguero, Org. Biomol. Chem., 2004, 2, 1587 DOI: 10.1039/B314742H

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