Tetrazene

Not to be confused with Tetrazine, Tetracene, or Tetrazene explosive.

Tetrazene

Names
IUPAC name (2E)-2-Tetraazene
Other names 2-Tetrazene
Identifiers
CAS Number	54410-57-0 (2-tetrazene) N
3D model (JSmol)	Interactive image
ChemSpider	4576001  Y
PubChem CID	5463295  (2-tetrazene)
CompTox Dashboard (EPA)	DTXSID00969547
InChI InChI=1S/H4N4/c1-3-4-2/h(H2,1,4)(H2,2,3); Y Key: MAZKAODOCXYDCM-UHFFFAOYSA-N Y
SMILES N/N=N/N
Properties
Chemical formula	H4N4
Molar mass	60.060 g·mol−1
Appearance	colorless
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Explosive
Related compounds
Related binary azanes	Ammonia Hydrazine Triazane
Related compounds	Diazene Triazene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

Tetrazene is a chemical compound with the molecular formula H₂N−N=N−NH₂. It is a colorless explosive material. An analogue is the organosilicon derivative (tms)₂N−N=N−N(tms)₂ where tms is trimethylsilyl. ^[1] Isomeric with tetrazene is ammonium azide.

Tetrazene explosive, commonly known simply as tetrazene, is used for sensitization of priming compositions.

Properties

Tetrazene has eleven isomers. ^[2] The most stable of these is the straight-chain 2-tetrazene (H₂N−N=N−NH₂), having a standard heat of formation at 301.3 kJ/mol. The eleven isomers can be arranged into three groups: straight-chain tetrazenes, four-membered cyclotetrazane, and three-membered cyclotriazanes. Each straight-chain tetrazene isomer possesses one N=N double bond and two N−N single bonds. ^[2] Tautomerizations do occur between the isomers. The ionic compound ammonium azide is also a constitutional isomer of tetrazene.

Organometallic derivatives

A variety of coordination complexes are known for R₂N2−4 (R = methyl, benzyl). ^[3]

References

1. Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. doi:10.1016/C2009-0-30414-6. ISBN   978-0-08-037941-8.
2. Li, L.-C.; Shang, J.; Liu, J.-L.; Wang, X.; Wong, N.-B. (2007). "A G3B3 study of N₄H₄ isomers". Journal of Molecular Structure. 807 (1–3): 207–10. doi:10.1016/j.theochem.2006.12.009.
3. Bowman, Amanda C.; Tondreau, Aaron M.; Lobkovsky, Emil; Margulieux, Grant W.; Chirik, Paul J. (2018). "Synthesis and Electronic Structure Diversity of Pyridine(diimine)iron Tetrazene Complexes". Inorganic Chemistry. 57 (16): 9634–9643. doi:10.1021/acs.inorgchem.8b00140. PMID   29620870.