Bond-alternated and bond-equalized hexazine derivatives.

Planar cyclic conjugated molecules satisfying the Hückel rule are generally classified as aromatics and π delocalization is the key feature of aromatic compounds. It was shown that the π system of benzene prefers bond-alternation and that the delocalization observed is a consequence of bond-equalization, which is a σ effect. For systems wherein the π bonds are strong, such as those between N atoms, the π-distortivity may outweigh the σ preference for bond-equalization.