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The Pentagonal‐Pyramidal Hexamethylbenzene Dication: The Many Shades of Coordination Chemistry at Carbon

A recent report of the crystal structure of the pentagonal‐pyramidal hexamethylbenzene dication C6(CH3)62+ by Malischewski and Seppelt [Angew. Chem. Int. Ed. 2017, 56, 368.] confirmed the structural proposal made in the first report of this compound in 1973 by Hogeveen and Kwant [Tetrahedron Lett. 1973, 14, 1665]. The widespread attention that this compound quickly gained led us to reinvestigate its electronic structure. Based on intrinsic bond orbital analysis, effective oxidation state analysis, ring current analysis and comparison to well established coordination complexes, we demonstrate that the central carbon atom behaves like a transition metal. The central (apical) carbon atom, although best described as a highly Lewis‐acidic carbon atom coordinated with an anionic cyclopentadienyl ligand, is also capable to act as an electron pair donor to a formal CH3+ group. The different roles of coordination chemistry are discussed.

Authors:   Johannes E. M. N. Klein, Remco W. A. Havenith, Gerald Knizia
Journal:   Chemistry - A European Journal
Year:   2018
Pages:   n/a
DOI:   10.1002/chem.201705812
Publication date:   17-Jan-2018
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