Induced aromaticity

The influence of counterions on the stabilization of three-, five-, and six-membered cyclic organic and organoboron systems was studied by the ab initio (MP2(full)/6-31 I+G**) and density functional (B3LYP/6-3 I I+G**) methods. The structures of molecular charge transfer molecular complexes formed by the interaction with counterions are predicted. A crucial role of counterions in the stabilization of aromatic systems that are unstable in themselves was revealed. Stabilization of these systems involves both charge transfer and covalent bonding.