Friday 8 January 2016

organic chemistry - Why can't antiaromatic compounds just escape planarity and become non-aromatic to avoid destabilization?


Why can't just all anti-aromatic systems lose planarity (and hence conjugation) and be non-aromatic like cyclooctatetraene ?


Would they not be more stable that way? Because anti-aromatic systems tend to be highly destabilized.


What can be a good working rule to predict whether an anti-aromatic system will remain anti-aromatic or whether it will somehow manage to lose planarity and become non-aromatic?




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