Изворни код странице 1-Diazidokarbamoil-5-azidotetrazol

{{Chembox-lat
| Name           = 
| ImageFile      = 1-Diazidocarbamoyl-5-azidotetrazole.png
| PIN            = ''N''-(5-Azido-1''H''-tetrazol-1-yl)carbonimidoyl diazide
| 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-->
| Section1       = {{Chembox Identifiers-lat
| CASNo = 1306278-47-6
| 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-]
| Abbreviations = AA
| 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-lat
| 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-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
| 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|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-lat
| 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 }}</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-lat
| 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-lat
| ShockSens = <0.25 J
| FrictionSens = <1 N
| DetonationV = 8960 m·s<sup>−1</sup>
  }}
| Section6       = 
| Section7       = {{Chembox Hazards-lat
| MainHazards = will unpredictably and violently detonate-Part of the nitrogen highly energetic compounds family.
| NFPA-H = 
| NFPA-F = 
| NFPA-R = 
| NFPA-S =
| ExploLimits =
  }}
}}

'''1-Diazidokarbamoil-5-azidotetrazol''', koji se često u šali naziva azidoazid azid,<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> je heterociklično neorgansko jedinjenje sa formulom 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}}</ref> To je veoma reaktivan i izuzetno osetljiv [[eksploziv]].

== Sinteza ==

'''1-Diazidokarbamoil-5-azidotetrazol''' je proizveden diazotizacijom triaminogvanidinijum hlorida sa [[natrijum nitrit]]om u ultra-prečišćenoj vodi.<ref name="Klapötke 2011" /> Druga sinteza koristi reakciju metateze između izocijanogen tetrabromida u [[aceton]]u i vodenog rastvora [[natrijum azid]]a.<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> Ovo prvo formira izocijanogen tetraazid, „otvoreni“ izomer C<sub>2</sub>N<sub>14</sub>, koji na sobnoj temperaturi brzo prolazi kroz ireverzibilnu reakciju ciklizacije da bi se formirao tetrazolni prsten.<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>

== Svojstva ==

Molekul C<sub>2</sub>N<sub>14</sub> je monociklični tetrazol sa tri azidne grupe. Ovaj oblik prstena je u ravnoteži sa izocijanogen tetraazidom, izomernom acikličnom strukturom za koju je dugo poznato da brzo cikliše do [[tetrazol]]a.<ref name="Banert"/>

To je jedno iz porodice azotnih jedinjenja visoke energije u kojima [[atom]]i [[azot]]a nemaju jake trostruke veze. Ova nestabilnost čini mnoga takva jedinjenja podložnim eksplozivnom raspadanju, oslobađajući gas [[azot]]a.

Ovaj tetrazolni [[eksploziv]] ima temperaturu raspadanja od {{convert|124|C|F K}}. Veoma je osetljiv, sa osetljivošću na udar nižom od 0,25 džula. Međutim, manje je osetljiv od azot trijodida. Razlaganje se može pokrenuti kontaktom ili korišćenjem laserskog zraka.<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> Iz ovih razloga, često se pogrešno tvrdi da je najosetljivije jedinjenje na svetu.<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"/>

== Reference ==
{{Reflist|2}}

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

{{Подножје|lat=da|Molekularna i ćelijska biologija|Hemija}}

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