1-Diazidocarbamoyl-5-azidotetrazole

1-Diazidocarbamoyl-5-azidotetrazole, often jokingly referred to as azidoazide azide,[5] is a heterocyclic inorganic compound with the formula C2N14.[6] It is a highly reactive and extremely sensitive explosive.

1-Diazidocarbamoyl-5-azidotetrazole
Names
Preferred IUPAC name
N-(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
ChemSpider
  • 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
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).
Infobox references

Synthesis

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

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 impact sensitivity lower than 0.25 Joules. It is, however, less sensitive than nitrogen triiodide. Decomposition can be initiated by 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]

See also

References
  1. "Azidoazide azide". American Chemical Society. 17 August 2020. Archived from the original on 28 October 2020. Retrieved 13 September 2021.
  2. Martin, Franz Albert. "Novel Energetic Materials based on 1,5-Diaminotetrazole and 3,5-Diamino-1H-1,2,4-triazole" (PDF). pp. 80–87. Archived (PDF) from the original on 16 April 2021. Retrieved 24 February 2018.
  3. US 2990412, Grundmann, Christoph J. & Schnabel, Wilhelm Joseph, "Isocyanogen tetraazide and its preparation", published 1961-06-27, assigned to Olin Mathieson Chemical Corp.
  4. Klapötke, Thomas M.; Martin, Franz A.; Stierstorfer, Jörg (26 April 2011). "C2N14: An Energetic and Highly Sensitive Binary Azidotetrazole". Angewandte Chemie International Edition. 50 (18): 4227–4229. doi:10.1002/anie.201100300. PMID 21472944.
  5. Lowe, Derek (9 January 2013). "Things I Won't Work With: Azidoazide Azides, More Or Less". Science Magazine. American Association for the Advancement of Science. Archived from the original on 7 May 2021. Retrieved 24 February 2018.
  6. Klapötke, Thomas M.; Martin, Franz A.; Stierstorfer, Jörg (26 April 2011). "C2N14: An Energetic and Highly Sensitive Binary Azidotetrazole". Angewandte Chemie International Edition. 50 (18): 4227–4229. doi:10.1002/anie.201100300. PMID 21472944.
  7. Banert, Klaus; Richter, Sebastian; Schaarschmidt, Dieter; Lang, Heinrich (2013). "Well Known or New? Synthesis and Structure Assignment of Binary C2N14 Compounds Reinvestigated". Angewandte Chemie International Edition. 52 (12): 3499–3502. doi:10.1002/anie.201209170. ISSN 1521-3773. PMID 23404921.
  8. Klapötke, Thomas M.; Krumm, Burkhard; Martin, Franz A.; Stierstorfer, Jörg (2011-11-09). "New Azidotetrazoles: Structurally Interesting and Extremely Sensitive". Chemistry: An Asian Journal. 7 (1): 214–224. doi:10.1002/asia.201100632. ISSN 1861-4728. PMID 22069147. S2CID 27239569.
  9. "Beware Of Azidoazide Azide, The World's Most Explosive Chemical". Discovery. Retrieved 2022-04-05.
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