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{{Chembox
{{Chembox
| Name =
| Name =
| ImageFile = C2N14.png
| ImageFile = 1-Diazidocarbamoyl-5-azidotetrazole.png
⚫
| PIN = ''N''-(5-Azido-1''H''-tetrazol-1-yl)carbonimidoyl diazide
| OtherNames = 5-Azido-1-diazidocarbamoyltetrazole<!-- Azidoazide azide is a joke name made up for the title of an article, not appropriate to list as an actual name for this chemical in encyclopediac tone -->
| OtherNames = {{ubl|1-Diazidocarbamoyl-5-azidotetrazole|5-Azido-1-diazidocarbamoyltetrazole|''N''-(5-Azido-1''H''-tetrazol-1-yl)carbonimidic diazide}}<!-- Azidoazide azide is a joke name made up for the title of an article, not appropriate to list as an actual name for this chemical in encyclopediac tone-->
⚫
| IUPACName = (5-Azido-1''H''-tetrazol-1-yl)carbonimidic diazide
⚫
| Section1 = {{Chembox Identifiers
| SystematicName = 1-Diazidocarbamoyl-5-azidotetrazole
| CASNo = 1306278-47-6
⚫
| Section1 = {{Chembox Identifiers
| CASNo_Ref = <ref>{{cite web |title=Azidoazide azide |url=https://www.acs.org/content/acs/en/molecule-of-the-week/archive/a/azidoazide-azide.html |website=American Chemical Society |language=en |date=17 August 2020 |access-date=13 September 2021 |archive-date=28 October 2020 |archive-url=https://web.archive.org/web/20201028181732/https://www.acs.org/content/acs/en/molecule-of-the-week/archive/a/azidoazide-azide.html |url-status=live }}</ref>{{Cascite|changed|}}
| PubChem = 101796054
| SMILES = N(=[N+]=[N-])C1=NN=NN1N=C(N=[N+]=[N-])N=[N+]=[N-]
| SMILES = N(=[N+]=[N-])C1=NN=NN1N=C(N=[N+]=[N-])N=[N+]=[N-]
| Abbreviations = AA
| Abbreviations = AA
| ChemSpiderID = 30649737
| ChemSpiderID = 30649737
| StdInChI = 1S/C2N14/c3-11-6-1(7-12-4)10-16-2(8-13-5)9-14-15-16
| StdInChIKey = ROKXTJDNIZBVDB-UHFFFAOYSA-N
}}
}}
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
| C=2 | N=14
| C=2 | N=14
| Density = 1.723 g·cm<sup>−3</sup><ref name="martin">{{cite web|last1=Martin|first1=Franz Albert|title=Novel Energetic Materials based on 1,5-Diaminotetrazole and 3,5-Diamino-1H-1,2,4-triazole|url=https://edoc.ub.uni-muenchen.de/14061/1/Martin_Franz_Albert.pdf|accessdate=24 February 2018|pages=80–87}}</ref>
| Density = 1.723 g·cm<sup>−3</sup><ref name="martin">{{cite web|last1=Martin|first1=Franz Albert|title=Novel Energetic Materials based on 1,5-Diaminotetrazole and 3,5-Diamino-1''H''-1,2,4-triazole|url=https://edoc.ub.uni-muenchen.de/14061/1/Martin_Franz_Albert.pdf|access-date=24 February 2018|pages=80–87|archive-date=16 April 2021|archive-url=https://web.archive.org/web/20210416094502/https://edoc.ub.uni-muenchen.de/14061/1/Martin_Franz_Albert.pdf|url-status=live}}</ref>
| MeltingPtC = 78
| MeltingPtC = 78
| BoilingPt = Violent explosion at 110 °C
| BoilingPt = Violent explosion at 110&nbsp;°C
| SolubleOther = Soluble in [[diethyl ether]], [[acetone]], hydrocarbons, chlorinated hydrocarbons<ref name="patent">{{Cite patent|title=Isocyanogen tetraazide and its preparation|gdate=1959-04-14|url=https://patents.google.com/patent/US2990412A/en}}</ref>
| SolubleOther = Soluble in [[diethyl ether]], [[acetone]], hydrocarbons, chlorinated hydrocarbons<ref name="patent">{{Cite patent|title=Isocyanogen tetraazide and its preparation|pubdate=1961-06-27|country=US|number=2990412|assign=[[Olin_Corporation|Olin Mathieson Chemical Corp.]]|inventor1-last=Grundmann|inventor1-first=Christoph J.|inventor2-last=Schnabel|inventor2-first=Wilhelm Joseph}}</ref>
}}
}}
| Section3 = {{Chembox Structure
| Section3 = {{Chembox Structure
⚫
| Structure_ref = <ref>{{cite journal |last1=Klapötke |first1=Thomas M. |last2=Martin |first2=Franz A. |last3=Stierstorfer |first3=Jörg |title=C<sub>2</sub>N<sub>14</sub>: An Energetic and Highly Sensitive Binary Azidotetrazole |journal=Angewandte Chemie International Edition |date=26 April 2011 |volume=50 |issue=18 |pages=4227–4229 |doi=10.1002/anie.201100300|pmid=21472944 |doi-access=free }}</ref>
| CrystalStruct = orthorhombic
| SpaceGroup = ''Pbcn''
| LattConst_a = 18.1289
| LattConst_b = 8.2128
| LattConst_c = 11.4021
| UnitCellVolume = 1697.6
| UnitCellFormulas = 8
}}
}}
| Section4 = {{Chembox Thermochemistry
| Section4 = {{Chembox Thermochemistry
| DeltaHf = 357 kcal·mol<sup>−1</sup><ref name="boom-town">{{cite web|last1=Lowe|first1=Derek|title=Things I Won't Work With: Azidoazide Azides, More Or Less|url=http://blogs.sciencemag.org/pipeline/archives/2013/01/09/things_i_wont_work_with_azidoazide_azides_more_or_less|work=Science Magazine|publisher=American Association for the Advancement of Science|accessdate=24 February 2018|date=9 January 2013}}</ref> (1495 kJ·mol<sup>−1</sup>)<ref name="martin"/>
| DeltaHf = 357 kcal·mol<sup>−1</sup><ref name="boom-town">{{cite web|last1=Lowe|first1=Derek|title=Things I Won't Work With: Azidoazide Azides, More Or Less|url=https://www.science.org/content/blog-post/things-i-won-t-work-azidoazide-azides-more-or-less|work=Science Magazine|publisher=American Association for the Advancement of Science|access-date=24 February 2018|date=9 January 2013|archive-date=7 May 2021|archive-url=https://web.archive.org/web/20210507110923/https://blogs.sciencemag.org/pipeline/archives/2013/01/09/things_i_wont_work_with_azidoazide_azides_more_or_less|url-status=live}}</ref> (1495 kJ·mol<sup>−1</sup>)<ref name="martin"/>
}}
}}
| Section5 = {{Chembox Explosive
| Section5 = {{Chembox Explosive
| ShockSens = <0.25 J
| ShockSens = <0.25 J
| FrictionSens = <1 N
| FrictionSens = <1 N
| DetonationV = 8960 m·s<sup>−1</sup>
| DetonationV = 8960 m·s<sup>−1</sup>
}}
}}
| Section6 =
| Section6 =
| Section7 = {{Chembox Hazards
| Section7 = {{Chembox Hazards
| MainHazards = will unpredictably and violently detonate
| MainHazards = will unpredictably and violently detonate-Part of the nitrogen highly energetic compounds family.
⚫
| ExploLimits =
⚫
| NFPA-F =
| NFPA-H =
| NFPA-H =
| NFPA-R = 4
| NFPA-F =
| NFPA-S =
| NFPA-R =
⚫
| NFPA-S =
⚫
| ExploLimits =

}}
}}
}}
}}
'''1-Diazidocarbamoyl-5-azidotetrazole''', often jokingly referred to as '''azidoazide azide''',<ref name="boom-town"/> is a [[Heterocyclic compound|heterocyclic]] [[Inorganic compound|inorganic]] compound with the formula C<sub>2</sub>N<sub>14</sub>.<ref name="Klapötke 2011">{{cite journal|last1=Klapötke|first1=Thomas M.|last2=Martin|first2=Franz A.|last3=Stierstorfer|first3=Jörg|title=C<sub>2</sub>N<sub>14</sub>: An Energetic and Highly Sensitive Binary Azidotetrazole|journal=Angewandte Chemie International Edition|date=26 April 2011|volume=50|issue=18|pages=4227–4229|doi=10.1002/anie.201100300|pmid=21472944|doi-access=free}}</ref> It is a highly reactive and [[Contact explosive|extremely sensitive]] [[explosive]].
{{Unreliable sources|date=December 2019}}
⚫
'''1-Diazidocarbamoyl-5-azidotetrazole''' is a [[Heterocyclic compound|heterocyclic]] [[Inorganic compound|inorganic]] compound with the formula C<sub>2</sub>N<sub>14</sub>.<ref name="Klapötke 2011">{{cite journal|last1=Klapötke|first1=Thomas M.|last2=Martin|first2=Franz A.|last3=Stierstorfer|first3=Jörg|title=C2N14: An Energetic and Highly Sensitive Binary Azidotetrazole|journal=Angewandte Chemie International Edition|date=26 April 2011|volume=50|issue=18|pages=4227–4229|doi=10.1002/anie.201100300|pmid=21472944}}</ref> It is an [[Contact explosive|extremely dangerous and sensitive]] [[explosive]], to the point of detonating from no obvious stimuli. This results in the near impossibility of conducting any sort of analysis of 1-diazidocarbamoyl-5-azidotetrazole.


== Synthesis ==
== Synthesis ==
1-Diazidocarbamoyl-5-azidotetrazole was produced by [[Diazonium compound|diazotizing]] triaminoguanidinium chloride with [[sodium nitrite]] in ultra-purified [[water]].<ref name="Klapötke 2011" /> Another synthesis uses a metathesis reaction between [[isocyanogen tetrabromide]] in [[acetone]] and aqueous [[sodium azide]].<ref name="patent" /> This first forms isocyanogen tetraazide, the "open" isomer of C<sub>2</sub>N<sub>14</sub>, which at room temperature quickly undergoes an irreversible cyclization reaction to form a [[tetrazole]] ring.<ref name="Banert">{{Cite journal|last1=Banert|first1=Klaus|last2=Richter|first2=Sebastian|last3=Schaarschmidt|first3=Dieter|last4=Lang|first4=Heinrich|date=2013|title=Well Known or New? Synthesis and Structure Assignment of Binary C<sub>2</sub>N<sub>14</sub> Compounds Reinvestigated|journal=Angewandte Chemie International Edition|volume=52|issue=12|pages=3499–3502|doi=10.1002/anie.201209170|pmid=23404921|issn=1521-3773}}</ref>
1-Diazidocarbamoyl-5-azidotetrazole was produced by [[diazotating]] triaminoguanidinium chloride with [[sodium nitrite]] in ultra-purified [[water]].<ref name="Klapötke 2011" />
:[[File:Isocyanogen tetraazide closure.png|300px]]


== Hazards ==
== Properties ==
The C<sub>2</sub>N<sub>14</sub> molecule is a monocyclic tetrazole with three [[azide]] groups. This ring form is in [[chemical equilibrium|equilibrium]] with isocyanogen tetraazide, an [[isomer]]ic acyclic structure that has long been known to cyclize quickly to the tetrazole.<ref name="Banert"/>
Nearly any stimulus, such as heat, radiation, or physical shock, will cause 1-diazidocarbamoyl-5-azidotetrazole to detonate.<ref>{{Cite journal|last=Klapötke|first=Thomas M.|last2=Krumm|first2=Burkhard|last3=Martin|first3=Franz A.|last4=Stierstorfer|first4=Jörg|date=2011-11-09|title=New Azidotetrazoles: Structurally Interesting and Extremely Sensitive|journal=Chemistry - an Asian Journal|volume=7|issue=1|pages=214–224|doi=10.1002/asia.201100632|pmid=22069147|issn=1861-4728}}</ref> It may also detonate unpredictably and for no apparent reason. When an attempt was made to chart its infrared spectrum using [[Raman spectroscopy]], it exploded.<ref name="boom-town" />


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.
However, at least two chemistry hobbyists have claimed to have produced the compound from [[isocyanogen tetrabromide]] and [[sodium azide]] following a 1959 patent<ref name="patent" /> and documented their results online. Preliminary qualitative observations suggested that although still highly sensitive, the compound is much less so than traditionally described, requiring moderate force to trigger a detonation.<ref name="ExplosionsAndFire 2019">{{cite web |url=https://www.youtube.com/watch?v=-Sz4d7RQB6Y |website=Youtube |accessdate=11 Aug 2019|title=I make C2N14 in my shed (azidoazide azide) - Ex&F}}</ref><ref name="&quot;messing&quot; with Azidoazide Azide">{{cite web |url=https://www.youtube.com/watch?v=OexBGncMwUY |website=YouTube |accessdate=19 February 2020|title="messing" with Azidoazide Azide}}</ref>{{Unreliable fringe source|date=December 2019}}


This tetrazole explosive has a decomposition temperature of 124&nbsp;°C. It is very sensitive, with an impact sensitivity lower than 0.25 joules. It is, however, less sensitive than [[nitrogen triiodide]]. Decomposition can be initiated by only using contact or using a laser beam.<ref>{{Cite journal|last1=Klapötke|first1=Thomas M.|last2=Krumm|first2=Burkhard|last3=Martin|first3=Franz A.|last4=Stierstorfer|first4=Jörg|date=2011-11-09|title=New Azidotetrazoles: Structurally Interesting and Extremely Sensitive|journal=Chemistry: An Asian Journal|volume=7|issue=1|pages=214–224|doi=10.1002/asia.201100632|issn=1861-4728|pmid=22069147|s2cid=27239569 }}</ref> For these reasons, it is often erroneously claimed to be the world's most sensitive compound.<ref>{{Cite web |title=Beware Of Azidoazide Azide, The World's Most Explosive Chemical |url=https://www.discovery.com/science/Azidoazide-Azide-Most-Explosive-Chemical |access-date=2022-04-05 |website=Discovery |language=en}}</ref><ref name="boom-town"/>
⚫
==References==
⚫
{{Reflist}}


==See also==
==See also==
* {{wiktionary-inline|azidoazide azide}}
* {{wiktionary-inline|azidoazide azide}}

⚫
==References==
⚫
{{Reflist}}

== External links ==
* {{youtube|uNhVK-2mh6w|Synthesis video}}
* {{youtube|E3Usu6SPVSg|Discussion between discoverer and hobby chemists about the synthesis video}}


{{DEFAULTSORT:Diazidocarbamoyl-5-azidotetrazole, 1-}}
{{DEFAULTSORT:Diazidocarbamoyl-5-azidotetrazole, 1-}}
[[Category:Tetrazoles]]
[[Category:Tetrazoles]]
[[Category:Azides]]
[[Category:Organoazides]]
[[Category:Explosives]]
[[Category:Explosive chemicals]]
[[Category:Explosive chemicals]]
[[Category:Inorganic carbon compounds]]
[[Category:Azines (hydrazine derivatives)]]

Latest revision as of 04:05, 16 September 2024

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).

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.

Synthesis

[edit]

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

[edit]

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. 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]

See also

[edit]

References

[edit]
  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 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. ^ a b c 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. ^ a b 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.
[edit]
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