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Anti-aromatic compounds are formed with a cyclic system of planar, overlapping p orbitals containing a non-Huckel number of electrons (i.e. not 4n+2 electrons -n being a natural number-). Non-aromatic compounds do not contain a continuously overlapping cyclic system of p orbitals. If a compound is antiaromatic, it is generally possible for the molecule to adopt a different conformation in order to disrupt the continual overlap of p orbitals. For example, 1,3,5,7-cyclooctatetraene, which would otherwise be antiaromatic, will adopt boat conformation to alleviate ring strain and antiaromaticity. 1,3,5,7-cyclooctatetrene Some molecules containing a lone pair or empty p-orbital can hybridize in order to eliminate anti aromaticity. What I don't understand is when a molecule will hybridize its lone pair or adopt a different conformation to become non-aromatic. Are non-aromatic compounds more stable than antiaromatic compounds all of the time? Will a molecule that is capable of bending or hybridizing it orbitals in order to avoid anti-aromaticity always do so, or are there special circumstances? Also, can an empty p orbital sp3 hybridize to render a compound non-aromatic?

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