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dc.contributor.authorZeng, Tao
dc.contributor.authorRawashdeh, Abdel Monem
dc.contributor.authorChakkingal Parambil, Priyakumari
dc.contributor.authorHoffmann, Roald
dc.date.accessioned2020-04-03T15:26:55Z
dc.date.available2020-04-03T15:26:55Z
dc.date.issued2017
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.identifier.urihttps://doi.org/10.1021/jacs.7b03388en_US
dc.identifier.urihttps://yorkspace.library.yorku.ca/xmlui/handle/10315/37163
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.language.isoenen_US
dc.publisherAmerican Chemical Societyen_US
dc.titleAn iodabenzene storyen_US
dc.typeArticleen_US
dc.rights.articlehttps://pubs.acs.org/doi/abs/10.1021/jacs.7b03388en_US


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