Jump to main content
Jump to site search

Issue 3, 2002
Previous Article Next Article

Möbius aromatic forms of 8-π electron heteropines

Author affiliations


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

Back to tab navigation

Supplementary files

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
  •   Request permissions

    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

Search articles by author