Diazo

Diazo refers to a type of organic compound called diazo compound that has two linked nitrogen atoms (azo) as a terminal functional group. The general formula is R₂C=N₂. The simplest example of a diazo compound is diazomethane. The electronic structure of diazo compounds involves a positive charge on the central nitrogen and negative charge distributed between the terminal nitrogen and the carbon. Some of the most stable diazo compounds are α-diazo-ß-diketones and α-diazo-ß-diesters since the negative charge is delocalized into the carbonyls. In contrast, most alkyldiazo compounds are explosive. A commercially relevant diazo compound is ethyl diazoacetate (N₂CHCOOEt). A group of isomeric compounds with only few similar properties are the diazirines, where the carbon and two nitrogens are linked as a ring.

Four resonance structures can be drawn:

Diazo compounds should not be confused with azo compounds of the type R-N=N-R or with diazonium compounds of the type R-N₂+.