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Closed Access item Homoheteroaromaticity: the case study of azepine and dibenzazepine

Authors:Dardonville, Christophe
Jimeno, M. Luisa
Alcorta, Ibon
Elguero, José
Keywords:1H-azepine, 5H-dibenz[b, f]azepine
Issue Date:2004
Publisher:Royal Society of Chemistry (Great Britain)
Citation:Organic and Biomolecular Chemistry 2 : 1587-1591 (2004)
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).
Publisher version (URL):http://dx.doi.org/10.1039/B314742H
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