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Issue 3, 2002
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Möbius aromatic forms of 8-π electron heteropines

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Abstract

Ab initio calculations at the B3LYP//6-31G(d) level predict that Möbius-like conformations of O, NF, S and PF-substituted 7-membered ring 8-π electron perfluoro-annulenes with an axis of symmetry exist, but they are of higher energy than isomers with a plane of symmetry. Chiral inversion of the Möbius perfluoroazepine system via a planar structure is shown to be an orbital symmetry forbidden process for a closed shell singlet state, resulting from the nodal characteristics of the highest occupied Möbius molecular orbital. The orbital origins of an unusual electron-correlation dependent lengthening predicted for the N–F bond in the Möbius conformation of the azepine but largely absent in the analogous phosphorus system are discussed. Structural variations based on incorporating a biphenyl motif are explored, but in no case was the Möbius form lower in energy than the achiral non-aromatic geometries retaining a plane of symmetry.

Graphical abstract: Möbius aromatic forms of 8-π electron heteropines

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Publication details

The article was received on 13 Dec 2001, accepted on 31 Jan 2002 and first published on 08 Feb 2002


Article type: Communication
DOI: 10.1039/B111369K
Citation: J. Chem. Soc., Perkin Trans. 2, 2002,0, 388-392
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    Möbius aromatic forms of 8-π electron heteropines

    W. L. Karney, C. J. Kastrup, S. P. Oldfield and H. S. Rzepa, J. Chem. Soc., Perkin Trans. 2, 2002, 0, 388
    DOI: 10.1039/B111369K

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