Homoaromaticity - Antihomoaromaticity

Antihomoaromaticity

There are also reports of antihomoaromatic compounds. Just as aromatic compounds exhibit exceptional stability, antiaromatic compounds, which deviate from Huckel's rule and contain a closed loop of 4n π electrons, are relatively unstable. The bridged bicycloocta-3,6-dien-2-yl cation contains only 4 π electrons, and is therefore "bishomoantiaromatic." A series of theoretical calculations confirm that it is indeed less stable than the corresponding allyl cation.

Similarly, a substituted bicycloocta-3,6-dien-2-yl cation (the 2-(4'-Fluorophenyl)bicyclooct-3,6-dien-2-yl cation) was also shown to be an antiaromate when compared to its corresponding allyl cation, corroborated by theoretical calculations as well as by NMR analysis.