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Tetrazene
Names
	IUPAC name (2E)-2-Tetraazene
	Other names (2E)-2-Tetraazen; Tetraaz-1-ene
Identifiers
CAS Number	54410-57-0 (2-tetrazene) ;
3D model (JSmol)	Interactive image;
ChemSpider	4576001 ;
PubChem CID	5463295 (2-tetrazene);
CompTox Dashboard (EPA)	DTXSID00969547 ;
	InChI InChI=1S/H4N4/c1-3-4-2/h(H2,1,4)(H2,2,3); Key: MAZKAODOCXYDCM-UHFFFAOYSA-N ;
	SMILES N/N=N/N;
Properties
Chemical formula	H4N4
Molar mass	60.060 g·mol−1
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). verify (what is ?) Infobox references

Tetrazene is a chemical compound with the molecular formula H₂NN=NNH₂. It is a colorless explosive material. An analogue is the organosilicon derivative (tms)₂NN=NN(tms)₂ where tms is trimethylsilyl.^[1] Isomeric with tetrazine 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 R₂N₄^2- (R = methyl, benzyl).^[3]

References

^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 978-0-08-037941-8.
^ ^a ^b 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.
^ 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.

[1] Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 978-0-08-037941-8.

[Li-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.

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