On the Stability of Large [4n]Annulenes
Organic Letters2003Vol. 5(17), pp. 2983–2986
Citations Over TimeTop 10% of 2003 papers
Chaitanya S. Wannere, Damian Moran, Norman L. Allinger, B. Andes Hess, L. J. Schaad, Paul von Ragué Schleyer
Abstract
[reaction: see text] The stabilization energies (B3LYP/6-31G) of planar [4n]annulenes, evaluated by a new indene-isoindene isomerization method (see Abstract graphic), reveal that all 4n pi-electron rings larger than the energetically unfavorable cyclobutadiene are only slightly destabilized by the pi-electron interactions. Cyclooctatetraene prefers the "tub" conformation because of strain effects. Generally, the antiaromatic character of the larger systems with 4n pi-electrons is revealed best by their magnetic properties rather than by their energies.
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