Abstract
AbstractWe describe the two‐electron reduction of N,N′‐dimethyl‐2,7‐diazapyrenium dications (MDAP2+), which afforded the corresponding reduced form (MDAP0) as a highly electron‐rich 16π antiaromatic system. A single‐crystal X‐ray diffraction analysis of MDAP0 revealed a distorted quinoidal structure with high bond‐length alternation. The 1H NMR spectrum of MDAP0 exhibited a diagnostic proton signal (4.6 ppm) that is distinctly upfield shifted compared to that of aromatic diazapyrene (8.3 ppm). Theoretical calculations supported the existence of a paratropic ring current. These results indicate that MDAP0 exhibits antiaromatic character derived from its peripheral 16π‐electron conjugation.
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