Charged paracyclophanes behave as annulenes with enhanced anisotropy

Paracyclophanes, in which benzene units are linked at the 1,4 positions by ethylene bridges (1-4), show annulene characteristics upon charging. The dependence of the magnetic properties of these charged rigid systems on the number of pi-electrons in the peripheries has been studied systematically. F...

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Bibliographic Details
Published inPerkin 2 : an international journal of physical organic chemistry Vol. 6; no. 6; pp. 1233 - 1241
Main Authors Shabtai, E, Segev, O, Beust, R, Rabinovitz, M
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2000
Subjects
Chemistry
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
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Summary:Paracyclophanes, in which benzene units are linked at the 1,4 positions by ethylene bridges (1-4), show annulene characteristics upon charging. The dependence of the magnetic properties of these charged rigid systems on the number of pi-electrons in the peripheries has been studied systematically. For the first time it can be shown that upon extensive reduction, two observable diatropic anionic stages exist (for 3). The results of advanced DFT calculations are in line with the experimental results. The limit on the number of pi-electrons in the periphery of annulenes, which still exhibit aromatic or anti-aromatic behavior, is extended far beyond the number of 26.
ISSN:0300-9580
1470-1820
1364-5471
DOI:10.1039/a909633g