1-Diazidocarbamoyl-5-azidotetrazole, often jokingly referred to as azidoazide azide,
is a
heterocyclic
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...
inorganic
In chemistry, an inorganic compound is typically a chemical compound that lacks carbon–hydrogen bonds, that is, a compound that is not an organic compound. The study of inorganic compounds is a subfield of chemistry known as ''inorganic chemist ...
compound with the formula C
2N
14.
It is an
extremely sensitive explosive
An explosive (or explosive material) is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An expl ...
.
Synthesis
1-Diazidocarbamoyl-5-azidotetrazole was produced by
diazotizing triaminoguanidinium chloride with
sodium nitrite
Sodium nitrite is an inorganic compound with the chemical formula NaNO2. It is a white to slightly yellowish crystalline powder that is very soluble in water and is hygroscopic. From an industrial perspective, it is the most important nitrite ...
in ultra-purified
water
Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as ...
.
Another synthesis uses a metathesis reaction between
isocyanogen tetrabromide in
acetone
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour.
Acetone is miscibl ...
and aqueous
sodium azide.
This first forms isocyanogen tetraazide, the "open" isomer of C
2N
14, which at room temperature quickly undergoes an irreversible cyclization reaction to form a
tetrazole ring.
Properties
The C
2N
14 molecule is a monocyclic tetrazole with three
azide
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 appli ...
groups with a molecular weight of 220.16 g.mol
−1. It has a molecular equilibrium between a closed and an open form, isocyanogen tetraazide which has been known since 1961, the latter being quickly cyclized to the cyclic tetrazole form (C
2N
14) at room temperature.
It is one of a family of high energy nitrogen compounds in which the nitrogen atoms do not have strong triple bonds. This conformation is less stable, making the compounds liable to explosive decomposition releasing
nitrogen
Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...
gas.
This tetrazole explosive has a decomposition temperature of 124 °C. It is very sensitive, with impact sensitivity lower than 0.25 Joules. It is, however, less sensitive than
nitrogen triiodide
Nitrogen triiodide is an inorganic compound with the formula N I3. It is an extremely sensitive contact explosive: small quantities explode with a loud, sharp snap when touched even lightly, releasing a purple cloud of iodine vapor; it can even ...
. Decomposition can be initiated by contact or using a laser beam. For these reasons, it is often erroneously claimed to be the world's most sensitive compound.
See also
*
References
External links
*
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{{DEFAULTSORT:Diazidocarbamoyl-5-azidotetrazole, 1-
Tetrazoles
Organoazides
Explosives
Explosive chemicals