Related Experiment Videos
On the stability of large [4n]annulenes
Chaitanya S Wannere1, Damian Moran, Norman L Allinger
1[reaction: see text] Computational Chemistry Annex, Department of Chemistry, University of Georgia, Athens, Georgia 30602, USA.
Organic Letters
|August 15, 2003
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.