Abstract
Abstract The stereochemical reactivities of monocyclic unsaturated compounds having 3–5 and 7–8 membered rings and of bicyclic pentalenes and heptalene can be rationalized through the bent bond/antiperiplanar hypothesis (BBAH) orbital model at the molecular level. This new orbital model considers unsaturations as Pauling τ bonds and that electron delocalization with adjacent pyramidal radical structures (derived from resonance structures) must strictly occur in antiperiplanar fashion. The BBAH shows that, contrary to aromatic (4n+2 Huckel) and nonaromatic molecules, antiaromatic molecules (4n Huckel) have adjacent double bonds that cannot conjugate through antiperiplanar electronic delocalization.
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