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Issue 17, 2016
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Centrohexaindane: six benzene rings mutually fixed in three dimensions – solid-state structure and six-fold nitration

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Abstract

The solid-state molecular structure of centrohexaindane (1), a unique hydrocarbon comprising six benzene rings clamped to each other in three dimensions around a neopentane core, and the molecular packing in crystals of 1·CHCl3 are reported. The molecular Td-symmetry and the Cartesian orientation of the six indane wings of 1 in the solid state have been confirmed. The course and limitation of electrophilic aromatic substitution of 1 are demonstrated for the case of nitration. Based on nitration experiments of a lower congener of 1, tribenzotriquinacene 5, the six-fold nitrofunctionalisation of 1 has been achieved in excellent yield, giving four constitutional isomers, two nonsymmetrical (14 and 17) and two C3-symmetrical ones (15 and 16), all of which contain one single nitro group in each of the six benzene rings. The relative yields of the four isomers (∼3 : 1 : 1 : 3) point to a random electrophilic attack of the electrophiles at the twelve formally equivalent outer positions of the aromatic periphery of 1, suggesting electronic independence of its six aromatic π-electron systems. In turn, the pronounced conformational rigidity of the centrohexacyclic framework of 1 enables the unequivocal structural identification of the isomeric hexanitrocentrohexaindanes 14–17 by 1H NMR spectroscopy.

Graphical abstract: Centrohexaindane: six benzene rings mutually fixed in three dimensions – solid-state structure and six-fold nitration

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Publication details

The article was received on 15 Nov 2015, accepted on 16 Dec 2015 and first published on 16 Dec 2015


Article type: Paper
DOI: 10.1039/C5CP07005H
Author version available: Download Author version (PDF)
Citation: Phys. Chem. Chem. Phys., 2016,18, 11722-11737
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    Centrohexaindane: six benzene rings mutually fixed in three dimensions – solid-state structure and six-fold nitration

    D. Kuck, J. Linke, L. C. Teichmann, D. Barth, J. Tellenbröker, D. Gestmann, B. Neumann, H. Stammler and H. Bögge, Phys. Chem. Chem. Phys., 2016, 18, 11722
    DOI: 10.1039/C5CP07005H

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