Resonance Structure of Diazonium Salts

The arenediazonium cation is stabilised by delocalisation of its positive charge over the aromatic ring: the terminal nitrogen's positive charge can be drawn as resonating onto the ring's ortho and para ring carbons through the conjugated pi system linking N=N to the ring, spreading the charge across several resonance structures rather than concentrating it on nitrogen alone. This dispersal of positive charge is what gives the arenediazonium salt its (relative, short-term) stability, in contrast to an aliphatic diaz …