An iodabenzene story
| dc.contributor.author | Zeng, Tao | |
| dc.contributor.author | Rawashdeh, Abdel Monem | |
| dc.contributor.author | Chakkingal Parambil, Priyakumari | |
| dc.contributor.author | Hoffmann, Roald | |
| dc.date.accessioned | 2020-04-03T15:26:55Z | |
| dc.date.available | 2020-04-03T15:26:55Z | |
| dc.date.issued | 2017 | |
| dc.description.abstract | 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. | en_US |
| dc.identifier.citation | A. 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.uri | https://doi.org/10.1021/jacs.7b03388 | en_US |
| dc.identifier.uri | https://hdl.handle.net/10315/37163 | |
| dc.language.iso | en | en_US |
| dc.publisher | American Chemical Society | en_US |
| dc.rights.article | https://pubs.acs.org/doi/abs/10.1021/jacs.7b03388 | en_US |
| dc.title | An iodabenzene story | en_US |
| dc.type | Article | en_US |