Stabilization of the Pseudo-Benzene N₆ Ring with Oxygen

The long sought N 6 ring that is isoelectronic with benzene can be formed by adding coordinate-covalent bonds from oxygen. Optimized structures, normal infrared harmonic frequencies, heats of formation, and activation energies for unimolecular dissociation are presented for the N 4 O, N 4 O 2, N 6 O, N 6 O 2, and N 6 O 3 systems. By increasing the number of oxygen atoms adjacent to the ring, a nitrogen ring with alternating positive and negative atomic charges can be created. In fact, the N 4 O 2 and N 6 O 3 systems have completely planar structures and computed heats of formation of 125.0 and 154.7 kcal mol -1, respectively. Furthermore, these systems appear kinetically stable with barriers to unimolecular dissociation of 44.8 and 62.4 kcal mol -1, respectively.