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In chemistry, an azide is the functional group N3, that is particularly useful for dipolar cycloaddition reactions, such as click chemistry reactions. Organic azides are readily formed by reacting sodium azide with halogenated alkanes. They can also be used as antibacterial agents.

Resonance Structures

The azide group is a linear molecule, and the most stable electron resonance structure is 1, depicted below, which contains four nitrogen-nitrogen bonds and low charge density. Two other resonance forms, 2 and 3, also contain four nitrogen-nitrogen bonds, but these structures are less stable due to the high charge density, 2^-, on one of the nitrogen atoms. Two additional resonance forms, 4 and 5, are also less stable because they contain only three nitrogen-nitrogen bonds.

Click Chemistry

Azides are frequently used to form cycloaddition products with alkynes under click chemistry reactions. Such chemistry is often used to synthesize triazole and tetrazole-based drugs.