1-Diazidocarbamoyl-5-azidotetrazole

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1-Diazidocarbamoyl-5-azidotetrazole.png
Names
Preferred IUPAC name
N-(5-Azido-1H-tetrazol-1-yl)carbonimidoyl diazide
Other names
  • 5-Azido-1-diazidocarbamoyltetrazole
  • N-(5-Azido-1H-tetrazol-1-yl)carbonimidic diazide
Identifiers
  • 1306278-47-6[1] ☒N
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
Lattice volume (V)
 1697.6
8
Thermochemistry
Std enthalpy of
formation (ΔfH⦵298)
 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
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

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

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 in acetone and aqueous sodium azide.[3] This first forms isocyanogen tetraazide, the "open" isomer of C2N14, which quickly cyclizes under standard conditions to form a tetrazole ring.[7]

Properties[]

The C2N14 molecule is a monocyclic tetrazole with three azide groups with a molecular weight of 220.16 g.mol−1. It has a molecular equilibrium between a closed and an open form, isocyanogen tetraazide which has been known since 1961, the latter being quickly cyclized to the cyclic tetrazole form (C2N14) at room temperature.[8]

It is one of a family of high energy nitrogen compounds in which the nitrogen atoms do not have strong triple bonds. This conformation is less stable, making the 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. Decomposition can be initiated by contact or using a laser beam.[9] Despite some exaggerated claims,[10] C2N14 is not the world's most sensitive compound; there are other contact explosives such as nitrogen triiodide which are much more sensitive.

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. ^ a b 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. ^ a b [1], "Isocyanogen tetraazide and its preparation", issued 1959-04-14  Archived 2021-04-17 at the Wayback Machine
  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. ^ a b 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. ^ a b 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. ^ Banert, K., Richter, S; Schaarschmidt, D, Lang, H (2013). "Well Known or New? Synthesis and Structure Assignment of Binary C2N14 Compounds Reinvestigated". Angewandte Chemie International Edition. 12 (52): 3499–3502. doi:10.1002/anie.201209170. PMID 23404921.
  9. ^ 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.
  10. ^ Explosions&Fire (2019-03-03). Making C2N14 from the hardware store - Azidoazide azide.

External links[]

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