1-Diazidocarbamoyl-5-azidotetrazole

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1-Diazidocarbamoyl-5-azidotetrazole
Names
Preferred IUPAC name
(5-Azido-1H-tetrazol-1-yl)carbonimidoyl diazide
Other names
  • 1-Diazidocarbamoyl-5-azidotetrazole
  • 5-Azido-1-diazidocarbamoyltetrazole
  • N-(5-Azido-1H-tetrazol-1-yl)carbonimidic diazide
Identifiers
3D model (JSmol)
Abbreviations AA[citation needed]
ChemSpider
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  • InChI=1S/C2N14/c3-11-6-1(7-12-4)10-16-2(8-13-5)9-14-15-16
    Key: ROKXTJDNIZBVDB-UHFFFAOYSA-N
  • N(=[N+]=[N-])C1=NN=NN1N=C(N=[N+]=[N-])N=[N+]=[N-]
Properties
C2N14
Molar mass 220.120 g·mol−1
Density 1.723 g·cm−3[2]
Melting point 78 °C (172 °F; 351 K)
Boiling point Violent explosion at 110 °C
Insoluble
Solubility Soluble in diethyl ether, acetone, hydrocarbons, chlorinated hydrocarbons[3]
Structure[4]
orthorhombic
Pbcn
a = 18.1289, b = 8.2128, c = 11.4021
1697.6
8
Thermochemistry
357 kcal·mol−1[5] (1495 kJ·mol−1)[2]
Explosive data
Shock sensitivity <0.25 J
Friction sensitivity <1 N
Detonation velocity 8960 m·s−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 will unpredictably and violently detonate – part of the nitrogen highly energetic compounds family.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1-Diazidocarbamoyl-5-azidotetrazole[a] is a heterocyclic inorganic compound with the formula C2N14.[6] It is a highly reactive and extremely sensitive explosive.

Synthesis

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1-Diazidocarbamoyl-5-azidotetrazole was produced by diazotizing triaminoguanidinium chloride with sodium nitrite in ultra-purified water.[6] Another synthesis uses a metathesis reaction between isocyanogen tetrabromide in acetone and aqueous sodium azide.[3] This first forms isocyanogen tetraazide, the "open" isomer of C2N14, which at room temperature quickly undergoes an irreversible cyclization reaction to form a tetrazole ring.[7]

Properties

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The C2N14 molecule is a monocyclic tetrazole with three azide groups. This ring form is in equilibrium with isocyanogen tetraazide, an isomeric acyclic structure that has long been known to cyclize quickly to the tetrazole.[7]

It is one of a family of high energy nitrogen compounds in which the nitrogen atoms do not have strong triple bonds. This instability makes many such compounds liable to explosive decomposition, releasing nitrogen gas.

This tetrazole explosive has a decomposition temperature of 124 °C. It is very sensitive, with an impact sensitivity lower than 0.25 joules. It is, however, less sensitive than nitrogen triiodide and 1,1'-azobis(1,2,3,4-tetrazole). Decomposition can be initiated by only using contact or using a laser beam.[8] For these reasons, it is often erroneously claimed to be the world's most sensitive compound.[9][5][10]

See also

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  • The dictionary definition of azidoazide azide at Wiktionary

Notes

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  1. ^ Sometimes jokingly referred to as azidoazide azide[5]

References

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  3. ^ a b US 2990412, Grundmann, Christoph J. & Schnabel, Wilhelm Joseph, "Isocyanogen tetraazide and its preparation", published Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Olin Mathieson Chemical Corp. 
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