Diazonium compound

Diazonium salts are a class of organic chemical compounds having the general structural formula: R -N2 X -. Here, R represents an organic, mostly aromatic radical dar. X is an unspecified anion. The simplest representatives of this group are the phenyldiazonium.

Aliphatic diazonium salts are often unstable. Upon heating ( thermolysis ) or irradiation (photolysis ) occur with elimination of nitrogen ( N2) carbenes.

Representation

Diazonium salts can be prepared by diazotization of primary aromatic amines with nitrite in acidic medium at low temperature.

Properties

Pure diazonium salts are unstable, explosive, and can usually only handle in aqueous solution ( at temperatures <5 ° C). They disintegrate when you try them free of water to get explosive, but can be customized with sterically suitable anions isolate partially.

Aromatic diazonium salts possess because of the resonance stabilization some resistance:

Use

Aqueous solutions of aromatic diazonium salts are used as intermediates in the synthesis of aromatic compounds, eg, by the Sandmeyer reaction and especially by azo coupling of azo dyes. In the diazotization of the chiral α -amino acids appear to diazonium salts as intermediates which react in aqueous solution stereoselectively to α -hydroxycarboxylic acids of the same configuration.