Energy Partitioning Analysis Research Articles

Boat and chair benzenes incorporated in cyclophanes

Various modes of the out-of-plane deformation of a benzene ring have been examined theoretically the MINDO/2 methods. Deformation to the boat conformation is predicted to be more facile than that to the half-boat or the chair conformation as observed in triple-layered[2.2]-metacyclophanes. The energy partitioning analysis reveals that a minimal loss of resonance energy at the gunwale of benzene boats appears to be responsible for the ease of boat deformations. The out-of-plane bending of the H atom at the bow of die benzene boats is coupled to the displacement of the H at the gunwale in such a way that the torsion of the bond between the bow and gunwale C atoms may be kept as small as possible.