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Synthesis and Crystal Structure of Nitrogen-rich Compound: 2,5,2′-triazido-1,1′-azo-1,3,4-triazole

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Abstract

The title compound 2,5,2′-triazido-1,1′-azo-1,3,4-triazole(2) has been synthesized by the reaction of 2,5,2′-trichloro-1,1′-azo-1,3,4-triazole(1) with sodium azide. Its crystal structure was determined by single-crystal X-ray diffraction. It crystallizes in triclinic, space group P−1 with a = 6.6604(13) Å, b = 6.7035(13) Å, c = 12.916 (3) Å, α = 98.13(3)°, β = 95.56(3)°, γ = 106.48° V = 541.68(18) Å3, Z = 2, C4HN17, Mr = 287.22, D c  = 1.761 g cm−3, F(000) = 288 and μ(MoKa) = 0.140 mm−1, the final R = 0.0553 and wR = 0.1541. X-ray analysis indicates a stronger delocalization of the azo π bond along the hypothetical N4 moiety within the title compound than those in(E)-1,2-bis(2,6-diazido-9- azabicyclo[3.3.1]nonan-9-yl)diazene.

Index abstract

The title compound 2,5,2′-triazido-1,1′-azo-1,3,4-triazole has been synthesized by the reaction of 2,5,2′-trichloro-1,1′-azo-1,3,4-triazole with sodium azide. Its crystal structure was determined by single-crystal X-ray diffraction. X-ray analysis indicates a stronger delocalization of the azo π bond along the hypothetical N4 moiety within the title compound than those in(E)-1,2-bis(2,6-diazido-9-azabicyclo[3.3.1] nonan-9-yl)diazene.

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References

  1. Huynh MHV, Hiskey MA, Archuleta JG (2004) Angew Chem Int Ed 43:5658–5661

    Article  CAS  Google Scholar 

  2. Ritter S (2004) Chem Eng News 82:24

    Google Scholar 

  3. Ye CF, Gao HX, Boatz JA (2006) Angew Chem Int Ed 45:7262–7265

    Article  CAS  Google Scholar 

  4. Huynh MHV, Hiskey MA, Archuleta JG (2005) Angew Chem Int Ed 44:737–739

    Article  CAS  Google Scholar 

  5. Gillan EG (2000) Chem Mater 12:3906–3912

    Article  CAS  Google Scholar 

  6. Sato T, Narazaki A, Kawaguchi Y, Niino H (2004) Appl Phys 79:1477–1479

    CAS  Google Scholar 

  7. Miller DR, Swenson DC, Gillan EG (2004) J Am Chem Soc 126:5372–5373

    Article  CAS  Google Scholar 

  8. Ali AN, Son SF, Hiskey MA, Naud DL (2004) J Propul Power 20:120–126

    Article  CAS  Google Scholar 

  9. Son SF, Berghout HL, Bolme CA, Chavez DE, Naud DL, Hiskey MA (2000) Proc Combust Inst 28:919–924

    Article  CAS  Google Scholar 

  10. Jadhav HS, Dhavale DD, Krishnamurthy VN (2001) Theory Pract Engerg Mater 4:493–504

    Google Scholar 

  11. Chavez DE, Hiskey MA, Naud DL (1999) J Pyrotech 10:17–36

    Google Scholar 

  12. Chavez DE, Hiskey MA (1998) J Pyrotech 7:11–14

    Google Scholar 

  13. Bennett G, Kolleck ML, Bennett JM (2003) Fire in the air. Military Aerosp Technol Dec 31

  14. Fallis S, Reed R, Lu Y-CF, Wierenga PH, Holland GF (2000) Proceedings of Halon Options Technical Working Conference. pp 361–370

  15. Xue H, Gao Y, Twamley B, Shreeve JM (2005) Chem Mater 17:191–198

    Article  CAS  Google Scholar 

  16. (a) Hammerl A, Klapötke TM (2002) Inorg Chem 41:906–912; (b) Hammerl A, Klapötke TM, Nolth H (2001) Inorg Chem 40:3570–3575; (c) Hammerl A, Klapötke TM, Mayer P (2005) Propellants Explos Pyrotech 30:17–24

  17. (a) Kebenich E, Klapötke TM, Knizek J, Noth H (1998) Eur J Inorg Chem 2013–2016; (b) Gillan EG (2000) Chem Mater 12:3906–3912

  18. Huynh MHV, Hiskey MA, Hartline EL (2004) Angew Chem Int Ed 43:4924–4928

    Article  CAS  Google Scholar 

  19. Chavez DE, Hiskey MA, Gilardi RD (2000) Angew Chem Int Ed 39:1791–1793

    Article  CAS  Google Scholar 

  20. (a) Huynh MHV, Hiskey MA, Archuleta JG (2004) Angew Chem Int Ed 116:5776–5779; (b) Huynh MHV, Hiskey MA, Chavez DE (2005) J Am Chem Soc 127:12537–12543; (c) Chavez DE, Hiskey MA, Gilardi RD (2004) Org Lett 6:2889–2991; (d) Li XT, Pang SP, Yu YZ (2007) Acta Chim Sin 10:971–975 (in Chinese)

  21. (a) Miller DR, Swenson DC, Gillan EG (2004) J Am Chem Soc 126:5372–5373; (b) Miller DR, Swenson DC, Gillan EG (2007) Inorg Chem 46:2767–2774

    Google Scholar 

  22. Naud DL, Hiskey MA, Harry HH (2003) J Energ Mater 21:57–62

    Article  CAS  Google Scholar 

  23. Bottaro JC (1999) US 5889161 (Chem Abstr 1999, 130:239630v)

  24. Li SH, Pang SP, Li XT, Yu YZ (2007) Chin Chem Lett 18:1176–1178

    Article  CAS  Google Scholar 

  25. Sheldrick DM (1997) SHELXS-97 and SHELXL-97. Program of crystal structure refinement. University of Göttingen, Germany

  26. Klapötke TM, Mayer P, Schulz A (2004) Propellants Explos Pyrotech 29:325–332

    Article  CAS  Google Scholar 

  27. Rose B, Schollmeyer D, Meier H (1997) Liebiegs Ann/Recueil 409–412

  28. Jiang WQ, Liu TB, Zou JP (2007) Chinese J Struct Chem 26:445–449

    CAS  Google Scholar 

Download references

Acknowledgements

We are grateful to the National Natural Science Foundation of China (No. 20772011 and 10576002) for financial support.

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Authors and Affiliations

  1. School of Material Science & Technology, Beijing Institute of Technology, Beijing, 100081, P. R. China

    Sheng-Hua Li, Cheng-Hui Sun, Xiao-Tong Li, Yong-Zhong Yu & Xin-Qi Zhao

  2. School of Life Science & Technology, Beijing Institute of Technology, Beijing, 100081, P. R. China

    Hong-Gang Shi & Si-Ping Pang

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Correspondence to Si-Ping Pang.

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Li, SH., Shi, HG., Sun, CH. et al. Synthesis and Crystal Structure of Nitrogen-rich Compound: 2,5,2′-triazido-1,1′-azo-1,3,4-triazole. J Chem Crystallogr 39, 13–16 (2009). https://doi.org/10.1007/s10870-008-9411-1

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