Tetrazene

Summary

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
2-Tetrazene.svg
Names
IUPAC name
(2E)-2-Tetraazene
Other names
(2E)-2-Tetraazen; Tetraaz-1-ene
Identifiers
  • 54410-57-0 (2-tetrazene) ☒N
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4576001 checkY
  • 5463295 (2-tetrazene)
  • DTXSID00969547 Edit this at Wikidata
  • InChI=1S/H4N4/c1-3-4-2/h(H2,1,4)(H2,2,3); checkY
    Key: MAZKAODOCXYDCM-UHFFFAOYSA-N checkY
  • N/N=N/N
Properties
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).
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Infobox references

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

PropertiesEdit

Tetrazene has eleven isomers.[2] The most stable of these is the straight-chain 2-tetrazene (H2-NN=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 derivativesEdit

A variety of coordination complexes are known for R2N42- (R = methyl, benzyl).[3]

ReferencesEdit

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