Azide

An alternative route is direct reaction of the metal with silver azide dissolved in liquid ammonia.

It reacts with epoxides, causing a ring-opening; it undergoes Michael-like conjugate addition to 1,4-unsaturated carbonyl compounds.

Azides have an ambivalent redox behavior: they are both oxidizing and reducing, as they are easily subject to disproportionation, as illustrated by the Frost diagram of nitrogen.

In 2005, about 251 tons of azide-containing compounds were annually produced in the world, the main product being sodium azide.

However, it has the disadvantage to be prone to trigger unexpected and undesirable side reactions that can jeopardize the experimental results.

[9][10][11] For example, the azide anion can oxidize pyrite (FeS2) with the formation of thiosulfate (S2O2−3), or reduce quinone into hydroquinone.

A proposed explanation is the stimulation of the denitrification processes because of the azide’s role in the synthesis of denitrifying enzymes.

[13] Moreover, azide also affects the absorbance and fluorescence optical properties of the dissolved organic matter (DOM) from soils.

[14] Many other interferences are reported in the literature for biochemical and biological analyses and they should be systematically identified and first rigorously tested in the laboratory before to use azide as microbial inhibitor for a given application.

As E°ox = -E°red, it gives the following series of oxidation reactions when the redox couples are presented as reductants: The azide functional group is commonly utilized in click chemistry through copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, where copper(I) catalyzes the cycloaddition of an organoazide to a terminal alkyne, forming a triazole.

Heavy-metal azides can accumulate under certain circumstances, for example, in metal pipelines and on the metal components of diverse equipment (rotary evaporators, freezedrying equipment, cooling traps, water baths, waste pipes), and thus lead to violent explosions.