1,1'-Azobis-1,2,3-triazole is a moderately explosive but comparatively stable
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
which contains a long continuous chain of
nitrogen
Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...
atoms, with an unbroken chain of eight nitrogen atoms cyclised into two
1,2,3-triazole
1,2,3-Triazole is one of a pair of isomeric chemical compounds with molecular formula CHN, called triazoles, which have a five-membered ring of two carbon atoms and three nitrogen atoms. 1,2,3-Triazole is a basic aromatic heterocycle.
Synthesis
...
rings. It is stable up to 194 °C. The compound exhibits
''cis''–''trans'' isomerism at the central
azo group: the ''trans''
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...
is more stable and is yellow, while the ''cis'' isomer is less stable and is blue. The two rings are
aromatic
In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...
and form a
conjugated system
In physical organic chemistry, a conjugated system is a system of connected p-orbitals with delocalized electrons in a molecule, which in general lowers the overall energy of the molecule and increases Chemical stability, stability. It is Reson ...
with the azo linkage. This
chromophore
A chromophore is the part of a molecule responsible for its color. The word is derived .
The color that is seen by our eyes is that of the light not Absorption (electromagnetic radiation), absorbed by the reflecting object within a certain wavele ...
allows the ''trans'' compound to be isomerised to the ''cis'' when treated with an appropriate
wavelength
In physics and mathematics, wavelength or spatial period of a wave or periodic function is the distance over which the wave's shape repeats.
In other words, it is the distance between consecutive corresponding points of the same ''phase (waves ...
of
ultraviolet
Ultraviolet radiation, also known as simply UV, is electromagnetic radiation of wavelengths of 10–400 nanometers, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight and constitutes about 10% of ...
light.
Related compounds
In 2011, 1,1'-azobis(1,2,3,4-tetrazole) with formula was prepared by
Klapötke and Piercey which has a 10-nitrogen chain. The record was later taken by a 11-nitrogen chain compound synthesized by a group of Chinese researchers. A branched chain of 11-nitrogen system has also been reported as part of
an unstable but highly nitrogen rich azidotetrazole derivative with formula .
See also
*
HBT (explosive)
HBT is a bistetrazole. It is an explosive approximately as powerful as HMX or CL-20, but it releases less toxic reaction products when detonated: ammonia and hydrogen cyanide
Hydrogen cyanide (formerly known as prussic acid) is a chemica ...
*
G2ZT
G2ZT is a bistetrazole. It is an explosive approximately as powerful as RDX, but it releases less toxic reaction products when detonated: ammonia and hydrogen cyanide
Hydrogen cyanide (formerly known as prussic acid) is a chemical compound ...
*
Diazene
Diimide, also called diazene or diimine, is a compound having the formula HN=NH. It exists as two geometric isomers, ''E'' (''trans'') and ''Z'' (''cis''). The term diazene is more common for organic derivatives of diimide. Thus, azobenzene is an ...
References
{{DEFAULTSORT:Azobis-1, 2, 3-triazole, 1, 1'-
Explosive chemicals
Triazoles
Azo compounds