Show simple item record

dc.contributor.authorZeng, Tao
dc.contributor.authorRawashdeh, Abdel Monem
dc.contributor.authorChakkingal Parambil, Priyakumari
dc.contributor.authorHoffmann, Roald
dc.identifier.citationA. M. Rawashdeh, P. C. Parambil, T. Zeng, R. Hoffmann. “An iodabenzene story.” Journal of the American Chemical Society 2017, 139, 7124-7129.en_US
dc.description.abstractWe call iodabenzene a cyclic (CH)5I molecule. A planar iodabenzene would have 8 π electrons, a situation best avoided by an out-of-plane distortion to a bird-like geometry. The electronic structure and charge distribution of this molecule resemble those of Meisenheimer complexes, derivatives of (CH)5CH2–. A similar substitution strategy, of π-acceptors in ortho and para positions, works in both cases to planarize and stabilize such derivatives. Some 40 kcal/mol (73 kcal/mol for the unsubstituted case) below the bird, a classical 5-iodocyclopentadiene structure awaits, reached through a bicyclic transition state. The calculated activation barrier for the highly exothermic reaction to a classical Lewis structure nevertheless make us optimistic about the chances of detecting and even isolating the bird isomer.en_US
dc.publisherAmerican Chemical Societyen_US
dc.titleAn iodabenzene storyen_US

Files in this item


This item appears in the following Collection(s)

Show simple item record

All items in the YorkSpace institutional repository are protected by copyright, with all rights reserved except where explicitly noted.