Substituent Effects and Structure in Substituted Dibenzonaphthyrones

Abstract

The crystal and molecular structures of [1]benzopyrano[4,3- c][1]benzopyran-5,11-done (dibenzo-naphthyrone) and three of its symmetrically tetrasubstituted derivatives have been determined by single-crystal X-ray diffraction methods. Only the tetra-t-butyl-substituted dibenzonaphthyrone was found to deviate significantly from planarity by having the two carbonyl groups folded and 'syn'-oriented relative to the plane of the connecting ethylene double bond. The dihedral angle between the two aromatic rings was found to be 25. The molecular geometry of all the other dibenzo-naphthyrones in their crystalline states is characterized by planarity, and their structures are centrosymmetric.