Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

An Iodabenzene Story

An Iodabenzene Story
Priyakumari Chakkingal Parambil, Tao Zeng, Roald Hoffmann, Abdel Monem Rawashdeh
We 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.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b03388

DOI: 10.1021/jacs.7b03388

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