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Monocyclic conjugated molecules have stabilities, bond lengths, and magnetic properties following expectations from Huckel's Rule. Two hydrocarbons which seem to deviate from these generalizations, s-indacene and cyclohepta(def)fluorene, were studied with density functional theory. The former has characteristics expected for both aromatic and antiaromatic molecules; the latter is a ground state triplet. Potentially aromatic transition states with 10 electrons were also investigated. The mechanism of the 5,5-sigmatropic shift is predicted to be stepwise involving diradical intermediates.

Theoretical studies of novel aromatic molecules and transition states