Triazene

Not to be confused with triazine.

Triazene
IUPAC name Triazene
Systematic name Triaz-1-ene[1]
Identifiers
CAS number	15056-34-5 Y
PubChem	115034
ChemSpider	102956 Y
ChEBI	CHEBI:35468
Gmelin Reference	49028
Jmol-3D images	Image 1
SMILES NN=N
InChI InChI=1S/H3N3/c1-3-2/h(H3,1,2) Y Key: AYNNSCRYTDRFCP-UHFFFAOYSA-N Y
Properties
Molecular formula	H3N3
Molar mass	45.04 g mol−1
Exact mass	45.032697111 gmol-1
Hazards
NFPA 704	4 3 4
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Triazene, also known as triazanylene, is an unsaturated inorganic compound having the chemical formula N₃H₃. It has one double bond, and is the second simplest member of the azene class of hydronitrogen compounds, and is not found in nature. It is also the name given to the functional group consisting of an amine directly bonding to an azo group, i.e. with the linkage R¹R²N-N=NR³ where R¹, R² and R³ are substituents. The functional group is also called a diazoamino group (but only one of the two substituents R¹ and R³ may be hydrogen) because it is related to a diazo group.

Properties

At room temperature, triazene is a gas, and as with many other azenes, it is also coloured with a strong and unpleasant smell. Triazene has a higher density and boiling point than diazene due to its greater size. It has a slightly lower boiling point than triazane and is thus more volatile. It has strong polar bonds, and the molecule has a large dipole moment due to its reduced symmetry.

Triazene has the same empirical formula as cyclotriazane but their atoms are connected in different ways, making these molecules structural isomers.

Production

To date, the only proven method to produce triazene, is the spontaneous decomposition of tetraazane into triazene and ammonia.

Derivatives

General structure of a triazene

A well known example is of a triazene is diphenyl derivative,^[2] PhNH-N=NPh (m.p. 100 °C, CAS #136-35-6). It is prepared from phenyldiazonium salts and aniline in the presence of base:

PhN₂⁺ + PhNH₂ → PhNHN=NPh + H⁺

See also

• Diazene
• Triphosphene

References

1. ^ triazene, Chemical Entities of Biological Interest
2. ^ Hartman, W. W.; Dickey, J. B. "Diazoaminobenzene" Organic Syntheses, Collected Volume 2, p.163 (1943). http://www.orgsyn.org/orgsyn/pdfs/CV2P0163.pdf

External links

• IUPAC Gold Book definition