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1,1'-Azobis-1,2,3-triazole

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1,1'-Azobis-1,2,3-triazole

trans-1,1'-Azobis-1,2,3-triazole (on top)
cis-1,1'-Azobis-1,2,3-triazole (on bottom)
  Carbon, C  Hydrogen, H  Nitrogen, N
Names
Preferred IUPAC name 1,1′-Diazenediyldi(1H-1,2,3-triazole)
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C4H4N8/c1-3-11(7-5-1)9-10-12-4-2-6-8-12/h1-4H/b10-9+Key: WUPZAQSKRMYJNB-MDZDMXLPSA-N
SMILES
  • c2cnnn2\N=N\n1ccnn1
Properties
Chemical formula C4H4N8
Molar mass 164.132 g·mol
Appearance Blue (cis isomer)
Yellow (trans isomer)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Explosive
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

1,1'-Azobis-1,2,3-triazole is a moderately explosive but comparatively stable chemical compound 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.

Related compounds

In 2011, 1,1'-azobis(1,2,3,4-tetrazole) with formula C2H2N10 was prepared by Klapötke and Piercey which has a 10-nitrogen chain. The record was later taken by a 11-nitrogen chain compound synthesized by a group of Chinese researchers. A branched chain of 11-nitrogen system has also been reported as part of an unstable but highly nitrogen rich azidotetrazole derivative with formula C2N14.

1,1′-Azobis(1,2,3,4-tetrazole) (trans isomer)

See also

References

  1. Li, Y. C.; Qi, C.; Li, S. H.; Zhang, H. J.; Sun, C. H.; Yu, Y. Z.; Pang, S. P. (2010). "1,1′-Azobis-1,2,3-triazole: A High-Nitrogen Compound with Stable N8 Structure and Photochromism". Journal of the American Chemical Society. 132 (35): 12172–3. doi:10.1021/ja103525v. PMID 20715773.
  2. Klapötke, Thomas M.; Piercey, Davin G. (2011). "1,1′-Azobis(tetrazole): A Highly Energetic Nitrogen-Rich Compound with a N10 Chain". Inorg. Chem. 50 (7): 2732–2734. doi:10.1021/ic200071q. PMID 21384800.
  3. Tang, Y.; Yang, H.; Wu, B.; Ju, X.; Lu, C.; Cheng, G. (2013). "Synthesis and Characterization of a Stable, Catenated N11Energetic Salt". Angewandte Chemie International Edition. 52 (18): 4875–7. doi:10.1002/anie.201300117. PMID 23554233.
  4. Klapötke, T. M.; Krumm, B.; Martin, F. A.; Stierstorfer, J. R. (2012). "New Azidotetrazoles: Structurally Interesting and Extremely Sensitive". Chemistry: An Asian Journal. 7 (1): 214–224. doi:10.1002/asia.201100632. PMID 22069147. S2CID 27239569.
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