The phenalenyl motif: a magnetic chameleon

Abstract

The 12π cation (3) and 14π anion (4) derived from the phenalenyl radical (2) support diatropic ("aromatic") perimeter ring currents, but isoelectronic replacement of the central atom by either boron (5) or nitrogen (6) leads to paratropic ("antiaromatic") current; the ipsocentric approach to molecular magnetic response accounts for all four patterns in terms of competition between translationally and rotationally allowed virtual π-π* excitations.