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Synthesis and Properties of the First Möbius Annulenes
Author(s) -
Ajami Dariush,
Hess Kirsten,
Köhler Felix,
Näther Christian,
Oeckler Oliver,
Simon Arndt,
Yamamoto Chiyo,
Okamoto Yoshio,
Herges Rainer
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600215
Subject(s) - annulene , möbius strip , planar , open shell , yield (engineering) , perimeter , twist , topology (electrical circuits) , chemistry , computational chemistry , physics , combinatorics , mathematics , geometry , computer science , organic chemistry , computer graphics (images) , thermodynamics
Heilbronner in 1964 predicted that annulenes with “… a planar perimeter of N =4 r AO's, which would yield an open shell configuration when occupied by 4 r electrons, can be twisted into a closed shell Möbius strip perimeter without loss in π electron energy”. We have been able to synthesize the first [4 n ]annulene with such a Möbius topology and now present further Möbius isomers and the details of their preparation as stable compounds. To address the question whether the twist in the π system has an effect on the properties we systematically investigate energy, geometry and magnetic parameters of a large number isomers of [16]annulenes. The Möbius twisted annulenes are consistently more aromatic than the non‐twisted isomers. This is true for the parent as well as our benzoannelated systems. Our results are in contrast to those published recently by C. Castro, W. L. Karney, P. von R. Schleyer et al.