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Issue 11, 2004
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Homoheteroaromaticity: the case study of azepine and dibenzazepine

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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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Publication details

The article was received on 17 Nov 2003, accepted on 26 Mar 2004 and first published on 11 May 2004


Article type: Paper
DOI: 10.1039/B314742H
Citation: 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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