Question

Why are aromatic diazonium salts more stable than aliphatic diazonium salts?

Answer 1

Aromatic and aliphatic diazonium salts:

1. Aliphatic diazonium salts exist only as short intermediates that rapidly decompose into nitrogen molecules and carbonium ions.
2. Certain aromatic diazonium salts are stable enough to be isolated but react easily with nitrogen loss or the formation of azo compounds.

Aromatic diazonium salts are more stable than aliphatic diazonium salts:

1. Aromatic diazonium salts exhibit resonance, which causes the positive charge to become dispersed.
2. In aliphatic diazonium salts, no similar resonance is seen.
3. Since they are more stable, aromatic diazonium salts are preferred to aliphatic diazonium salts.
4. due to structural representation or resonance-stabilizing features.
5. Due to resonance-induced positive charge dispersion over the benzene ring, aromatic diazonium salts are more stable than aliphatic diazonium salts.