para-benzynes. Other studied biradicals are those based on pleiadene, extended viologens, corannulenes, nitronyl-nitroxide, bis(phenalenyl)s and teranthenes. Pleiadene has been synthesised from acenaphthylene and anthranilic acid / amyl nitrite: Oxyallyl The oxyallyl diradical (OXA) is a trimethylenemethane molecule with one methylene group replaced by oxygen. This reactive intermediate is postulated to occur in ring opening of cyclopropanones, allene oxides and in the Favorskii rearrangement. The intermediate has been produced by reaction of oxygen radical anions with acetone and studied by photoelectron spectroscopy. The experimental electron affinity of OXA is 1.94 eV. Classification Non-Kekulé molecules with two formal radical centers (non-Kekulé diradicals) can be classified into non-disjoint and disjoint by the shape of their two non-bonding molecular orbitals (NBMOs). Both NBMOs of molecules with non-disjoint characteristics such as trimethylenemethane have electron density at the same atom. According to Hund's rule, each orbital is filled with one electron with parallel spin, avoiding the Coulomb repulsion by filling one orbital with two electrons. Therefore, such molecules with non-disjoint NBMOs are expected to prefer a triplet ground state. In contrast, the NBMOs of the molecules with disjoint characteristics such as tetramethyleneethane can be described without having electron density at the same atom. With such MOs, the destabilization factor by the Coulomb repulsion becomes much smaller than with non-disjoint type molecules, and therefore the relative stability of the singlet ground state to the triplet ground state will be nearly equal, or even reversed because of exchange interaction. References Organic chemistry Free radicals