Magnetic Antiaromaticity─Paratropicity─Does Not Necessarily Imply Instability.

Magnetically induced ring currents are a conventional tool for the characterization of aromaticity. Dia- and paratropic currents are thought to be associated with stabilization (aromaticity) and destabilization (antiaromaticity), respectively. In the present work, I have questioned the validity of the paratropic currents as a measure of antiaromaticity among monocyclic hydrocarbons. I have shown that while reduced/oxidized radical ions of hydrocarbons sustain strong paratropic currents, they often gain extra stabilization via cyclic conjugation compared to their acyclic counterparts.