Article
Article
Diazotization
Article By:
Moore, James Alexander Department of Chemistry, University of Delaware, Newark, Delaware.
Last reviewed:January 2020
DOI:https://doi.org/10.1036/1097-8542.191900
The process by which an aromatic primary amine is converted to a diazonium compound. The preparation and reactions of diazonium salts were discovered in 1858 and were the basis of the synthetic dye industry and the development of other industrial chemistry in Europe. In diazotization, sodium nitrite is added to a solution of the amine in aqueous acid solution at 0–5°C (32–41°F). Reaction of the amine with nitrous acid gives a nitrosamine. Tautomerization and loss of water lead to the diazonium ion, which is stabilized by delocalization of the positive charge at the ortho and para carbon atoms of the ring [reaction (1)].
(1)
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