Lemniscular Hexaphyrins as Examples of Aromatic and Antiaromatic Double-Twist Möbius Molecules

Henry S. Rzepa*
Department of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ
Org. Lett., 2008, 10 (5), pp 949–952
DOI: 10.1021/ol703129z
Publication Date (Web): February 9, 2008
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, h.rzepa@imperial.ac.uk
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Abstract

Two reported [26] and [28]hexaphyrins are analyzed via measured and computed geometries and NMR-shieldings as examples of respectively 4n + 2 π-electron aromatic and 4n π-electron antiaromatic double-twist Möbius ring systems, adopting a lemniscular/figure-eight topology with linking number LK = 2π. Values of local twist (TW) and nonlocal writhe (WR) derived from the relation Lk = Tw + WR appear relatively insensitive to the aromatic/antiaromatic character. The [26]hexaphyrin may adopt differing solution and solid-state conformations.

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History

  • Published In Issue March 06, 2008
  • Received December 30, 2007

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