Quantifying electron delocalization in orthogonal channels: Theoretical investigation of σ and π aromaticity in [C6I6]2+ and [C6Cl6]2+

The properties of the hexaiodobenzene dication are analyzed using DFT since this simple molecular system can be considered as the simplest prototype to demonstrate toroidal delocalization at the periphery of a benzene core. Electron delocalization is here quantified computing nucleus independent chemical shift.