Question

Account for the following: Diazonium salts of aromatic amines are more stable than those of aliphatic amines?

Answer 1

Diazonium salts:

• Diazonium compounds or diazonium salts are known as the group of organic compounds having a functional group ${\mathrm{RN}}^{+}\mathrm{X}⁻$ where $\mathrm{R}$ can be denoted as any organic group i.e Alkyl or an Aryl, however, $\mathrm{X}$ is denoted as an inorganic or organic anion i.e Halogen.

Diazonium salts of aromatic amines are more stable than those of Aliphatic amines:

• In the case of the Aromatic diazonium salts, there is the dispersal of a positive charge is on the benzene ring resulting from resonance.
• In other words, the stability of the Diazonium salt of aromatic amine results from the resonance, where the aromatic rings carry an N atom with a positive charge.
• The resonating structure for the Diazonium salts of Aromatic amines can be shown as:

• Whereas in the case of Diazonium salts of the Aliphatic amines such delocalization is not possible which makes them less stable.

Hence, diazonium salts of aromatic amines are known to be more stable than those of aliphatic amines.