Abstract
It has been postulated that the title compound, C 14 H 9 NO, (1a), may play a role in idiosyncratic reactions induced by carbamazepine, one of the most widely used anticonvulsants in North America. Compound (1a) was found to be nearly planar, unlike its parent compound iminostilbene. The possibility of the azepinone having a resonance contribution from the novel nitrenium ion was investigated. The slightly elongated C=N and C=O bond lengths suggest that there is some contribution from the nitrenium structure. However, the alternating bond lengths show that the major resonance contributor is the iminoquinone.
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