1,1'-Azobis-1,2,3-triazole
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| verifiedrevid = 442660798
| ImageFile=1,1'-Azobis-1,2,3-triazole.svg
| ImageSize=200px
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| ImageFile2=1,1%27-Azobis-1,2,3-triazole-3D.png
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| ImageCaption2 = trans-1,1'-Azobis-1,2,3-triazole (on top)
cis-1,1'-Azobis-1,2,3-triazole (on bottom)
{{legend|black|Carbon, C}}{{legend|white|Hydrogen, H}}{{legend|blue|Nitrogen, N}}
| PIN=1,1{{prime}}-Diazenediyldi(1H-1,2,3-triazole)
|Section1={{Chembox Identifiers
| CASNo=1354420-07-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = M7A5U2N4ZU
| PubChem=71308130
| SMILES=c2cnnn2\N=N\n1ccnn1
| StdInChI=1S/C4H4N8/c1-3-11(7-5-1)9-10-12-4-2-6-8-12/h1-4H/b10-9+
| StdInChIKey = WUPZAQSKRMYJNB-MDZDMXLPSA-N
| ChemSpiderID = 26234930
| ChemSpiderID1 = 26234931
}}
|Section2={{Chembox Properties
| C=4|H=4|N=8
| Appearance=Blue (cis isomer)
Yellow (trans isomer)
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|Section3={{Chembox Hazards
| MainHazards=Explosive
| FlashPt=
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|Section8={{Chembox Related
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1,1'-Azobis-1,2,3-triazole is a moderately explosive but comparatively stable chemical compound{{citation needed|date=May 2015}} which contains a long continuous chain of nitrogen atoms, with an unbroken chain of eight nitrogen atoms cyclised into two 1,2,3-triazole rings. It is stable up to 194 °C. The compound exhibits cis–trans isomerism at the central azo group: the trans isomer is more stable and is yellow, while the cis isomer is less stable and is blue. The two rings are aromatic and form a conjugated system with the azo linkage. This chromophore allows the trans compound to be isomerised to the cis when treated with an appropriate wavelength of ultraviolet light.{{Cite journal | last1 = Li | first1 = Y. C. | last2 = Qi | first2 = C. | last3 = Li | first3 = S. H. | last4 = Zhang | first4 = H. J. | last5 = Sun | first5 = C. H. | last6 = Yu | first6 = Y. Z. | last7 = Pang | first7 = S. P. | doi = 10.1021/ja103525v | title = 1,1{{prime}}-Azobis-1,2,3-triazole: A High-Nitrogen Compound with Stable N8 Structure and Photochromism | journal = Journal of the American Chemical Society | volume = 132 | issue = 35 | pages = 12172–3 | year = 2010 | pmid = 20715773}}
Image:AZBTcistrans.png{{clear left}}
Related compounds
In 2011, 1,1'-azobis(1,2,3,4-tetrazole) with formula {{chem2|C2H2N10}} was prepared by Klapötke and Piercey which has a 10-nitrogen chain.{{cite journal|title = 1,1{{prime}}-Azobis(tetrazole): A Highly Energetic Nitrogen-Rich Compound with a N10 Chain|last1 = Klapötke|first1 = Thomas M.|last2 = Piercey|first2 = Davin G.|journal = Inorg. Chem.|year = 2011|volume = 50|issue = 7|pages = 2732–2734|doi = 10.1021/ic200071q|pmid = 21384800}} The record was later taken by a 11-nitrogen chain compound synthesized by a group of Chinese researchers.{{Cite journal | last1 = Tang | first1 = Y. | last2 = Yang | first2 = H. | last3 = Wu | first3 = B. | last4 = Ju | first4 = X. | last5 = Lu | first5 = C. | last6 = Cheng | first6 = G. | doi = 10.1002/anie.201300117 | title = Synthesis and Characterization of a Stable, Catenated N11Energetic Salt | journal = Angewandte Chemie International Edition | volume = 52 | issue = 18 | pages = 4875–7 | year = 2013 | pmid = 23554233}}{{which|date=December 2023}} A branched chain of 11-nitrogen system has also been reported as part of an unstable but highly nitrogen rich azidotetrazole derivative with formula {{chem2|C2N14}}.{{Cite journal | last1 = Klapötke | first1 = T. M. | last2 = Krumm | first2 = B. | last3 = Martin | first3 = F. A. | last4 = Stierstorfer | first4 = J. R. | title = New Azidotetrazoles: Structurally Interesting and Extremely Sensitive | doi = 10.1002/asia.201100632 | journal = Chemistry: An Asian Journal | volume = 7 | pages = 214–224 | year = 2012 | issue = 1 | pmid = 22069147| s2cid = 27239569}}
Image:1,1′-azobis(tetrazole).png{{clear left}}
See also
References
{{Reflist}}
{{DEFAULTSORT:Azobis-1, 2, 3-triazole, 1, 1'-}}