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Concept
Azide
Summary
In chemistry, azide is a linear, polyatomic anion with the formula and structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the formula , containing the azide functional group. The dominant application of azides is as a propellant in air bags.
Sodium azide is made industrially by the reaction of nitrous oxide, with sodium amide in liquid ammonia as solvent:
Many inorganic azides can be prepared directly or indirectly from sodium azide. For example, lead azide, used in detonators, may be prepared from the metathesis reaction between lead nitrate and sodium azide. An alternative route is direct reaction of the metal with silver azide dissolved in liquid ammonia. Some azides are produced by treating the carbonate salts with hydrazoic acid.
Azide is isoelectronic with carbon dioxide , cyanate , nitrous oxide , nitronium ion and cyanogen fluoride NCF. Per valence bond theory, azide can be described by several resonance structures; an important one being
Azide salts can decompose with release of nitrogen gas. The decomposition temperatures of the alkali metal azides are: (275 °C), (355 °C), (395 °C), and (390 °C). This method is used to produce ultrapure alkali metals:
Protonation of azide salts gives toxic hydrazoic acid in the presence of strong acids:
Azide as a ligand forms numerous transition metal azide complexes. Some such compound are more shock sensitive.
Many inorganic covalent azides (e.g., chlorine, bromine, and iodine azides) have been described.
The azide anion behaves as a nucleophile; it undergoes nucleophilic substitution for both aliphatic and aromatic systems. It reacts with epoxides, causing a ring-opening; it undergoes Michael-like conjugate addition to 1,4-unsaturated carbonyl compounds.
Azides can be used as precursors of the metal nitrido complexes by being induced to release , generating a metal complex in unusual oxidation states (see high-valent iron).
Azides decompose with nitrite compounds such as sodium nitrite when acidified.
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