Welcome to Journal of Beijing Institute of Technology
Advance Search
Volume 21Issue 3
.
Turn off MathJax
Article Contents
Article Navigation> JOURNAL OF BEIJING INSTITUTE OF TECHNOLOGY> 2012> 21(3): 421-426
LI Ya-yu, PANG Si-ping, SUN Cheng-hui, LI Sheng-hua. Synthesis and crystal structure of a nitrogen-rich compound: 3,5-diazido-1,2,4-triazole[J]. JOURNAL OF BEIJING INSTITUTE OF TECHNOLOGY, 2012, 21(3): 421-426.
Citation: LI Ya-yu, PANG Si-ping, SUN Cheng-hui, LI Sheng-hua. Synthesis and crystal structure of a nitrogen-rich compound: 3,5-diazido-1,2,4-triazole[J].JOURNAL OF BEIJING INSTITUTE OF TECHNOLOGY, 2012, 21(3): 421-426.
shu

Synthesis and crystal structure of a nitrogen-rich compound: 3,5-diazido-1,2,4-triazole

  • School of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, China

  • Received Date:2011-11-17
    Abstract
  • The compound of 3,5-diazido-1,2,4-triazole was synthesized by the reaction of 2,5,2',5'-tetrachloro-1,1'-azo-1,3,4-triazole with sodium azide at 50℃. Its crystal structure was determined by single-crystal X-ray diffraction. It crystallizes in monoclinic, space group Cc with a=1.212 4(2) nm, b=2.342 4(5) nm, c=0.804 74(16) nm, β=125.56(3)°, V=1.859 3(6) nm 3, Z=4, C 2HN 9, Mr=151.04, D c=1.62 g/cm 3, F=(000)912 and μ(Mo Ka)=0.129 mm -1, the final R=0.039 7 and wR=0.087 4. X-ray analysis indicates a stronger intermolecular hydrogen bonding, leading to the formation of a trimmer, containing a nine-membered cyclic ring with graph-set R 3 3(9) in the compound.
    • FullText(HTML)
  • loading
    • References (34)
  • [1]
    Huynh M H V, Hiskey M A, Chavez D E, et al. Synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C-N compound [J]. Journal of American Chemical Society, 2005, 127: 12537-12543.
    [2]
    Joo Y H, Shreeve J M. Energetic mono-, di-, and trisubstituted nitroiminotetrazoles [J]. Angewandte Chemie International Edition, 2009, 48: 564-566.
    [3]
    KlapÖtke T M, Mayer P, Schulz A, et al. 1,5-Diamino-4-methyltetrazolium dinitramide [J]. Journal of American Chemical Society, 2005, 127: 2032-2037.
    [4]
    Sato T, Narazaki A, Kawaguchi Y, et al. Dicyanocarbodiimide and trinitreno-s-triazine generated by consecutive photolysis of triazido-s-triazine in a low-temperature nitrogen matrix [J]. Angewandte Chemie International Edition, 2003, 42: 5206-5208.
    [5]
    Chavez D E, Hiskey M A, Gilardi R D, et al. 3,3'-Azobis(6-amino-1,2,4,5-tetrazine): a novel high-nitrogen energetic material [J]. Angewandte Chemie International Edition, 2000, 39: 1791-1973.
    [6]
    Ye C F, Gao H X, Boatz J A, et al. Polyazidopyrimidines: high-energy compounds and precursors to carbon nanotubes [J]. Angewandte Chemie International Edition, 2006, 45: 7262-7265.
    [7]
    Xue H, Gao Y, Twamley B, et al. New energetic salts based on nitrogen-containing heterocycles [J]. Chemical Materials, 2005, 17: 191-195.
    [8]
    Hammerl A, KlapÖtke T M. Tetrazolylpentazoles: nitrogen-rich compounds [J]. Inorganric Chemistry, 2005, 41: 906-909.
    [9]
    Hammerl A, KlapÖtke T M, Nolth H, et al. +2N—CN 4] 2-: a new high-nitrogen high-energetic material [J]. Inorganric Chemistry, 2001, 40: 3570-3574.
    [10]
    Hammerl A, KlapÖtke T M, Mayer P, et al. Synthesis, structure, molecular orbital calculations and decomposition mechanism for tetrazolylazide CHN 7, its phenyl derivative PhCN 7and tetrazolylpentazole CHN 9[J]. Propellants Explosive Pyrotechnical, 2005, 30: 17-20.
    [11]
    Kebenich E, KlapÖtke T M, Knizek J, et al. Characterization, crystal structure of 2,4-bis(triphenylphosphanimino)tetrazolo - triazine, and improved crystal structure of 2,4,6-triazido-1,3,5-triazine[J]. European Journal of Inorganic Chemistry, 1998, 12: 2013-2016.
    [12]
    Gillan E G. Synthesis of nitrogen-rich carbon nitride networks from an energetic molecular azide precursor[J]. Chemical Materials, 2000, 12: 3906-3908.
    [13]
    Huynh M H V, Hiskey M A, Hartline E L, et al. Polyazido high-nitrogen compounds: hydrazo-and azo-1,3,5-triazine [J]. Angewandte Chemie International Edition, 2004, 43: 4924-4928.
    [14]
    Chavez D E, Hiskey M A, Gilardi R D, et al. 3,3'-Azobis(6-amino-1,2,4,5-tetrazine): a novel high-nitrogen energetic material [J]. Angewandte Chemie International Edition, 2000, 39: 1791-1794.
    [15]
    Huynh M H V, Hiskey M A, Archuleta J G, et al. 3,6-Di(azido)-1,2,4,5-tetrazine: a precursor for the preparation of carbon nanospheres and nitrogen-rich carbon nitrides [J]. Angewandte Chemie International Edition, 2004, 116: 5776-5778.
    [16]
    Huynh M H V, Hiskey M A, Chavez D E, et al. Synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C—N compound [J]. Journal of American Chemical Society, 2005, 127: 12537-12541.
    [17]
    Chavez D E, Hiskey M A, Gilardi R D, et al. Novel high-nitrogen materials based on nitroguanyl-substituted tetrazines [J]. Organic Letter, 2004, 6: 2889-2892.
    [18]
    Li Xiaotong, Pang Siping, Yu Yongzhong, et al. Synthesis and theoretical studies 3,6-diazido-1,2,4,5-tetrazine [J]. Acta Chimica Sinica, 2007, 10: 971-973. ( in Chinese)
    [19]
    Miller D R, Swenson D C, Gillan E G, et al. Synthesis and structure of 2,5,8-triazido-s-heptazine: an energetic and luminescent precursor to nitrogen-rich carbon nitrides [J]. Journal of American Chemical Society, 2004, 126: 5372-5376.
    [20]
    Miller D R, Swenson D C, Gillan E G, et al. Nitrogen-rich carbon nitride network materials via the thermal decomposition of 2,5,8-triazido-s-heptazine[J]. Inorganic Chemistry, 2007, 46: 2767-2771.
    [21]
    Huynh M H V, Hiskey M A, Archuleta J G, et al. 3,6-Di(azido)-1,2,4,5-tetrazine: a precursor for the preparation of carbon nanospheres and nitrogen-rich carbon nanospheres and nitrogen-rich carbon nitrides [J]. Angewandte Chemie International Edition, 2001, 43: 5658-5661.
    [22]
    Huynh M H V, Hiskey M A, Archuleta J G, et al. Preparation of nitrogen-rich nanolayered, nanoclustered, and nanodendritic carbon nitrides [J]. Angewandte Chemie International Edition, 2005, 44: 737-741.
    [23]
    Kerth J, Lobbecke S. Synthesis and characterization of 3,3'-Azobis(6-amino-1,2,4,5-tetrazine) DAAT-a new promising nitrogen-rich compound [J]. Propellants Explosive Pyrotechnical, 2002, 27:111-116.
    [24]
    Pevzner M S, Martynova M N. Trifluoromethyl-or pentafluorosulfanyl-substituted poly-1,2,3-triazole. Khim Geterotsikl Soedin, 1974, 9:1288-1290.
    [25]
    Li S H, Shi H G, Sun C H, et al. Synthesis and crystal structure of 2,2',5,5'-tetrachloro-1,1'-azo-1,3,4-triazole [J]. Journal of Chemical Crystallography, 2009, 39:13-15.
    [26]
    Li Shenghua,, Shi Honggang, Sun Chenghu, et al. Synthesis and crystal structure of novel highly nitrogen-containing compound of polyazidotriazole [J]. Chinese Journal of Organic Chemistry, 2008, 28: 727-729. (in Chinese)
    [27]
    Li S H, Pang S P, Li X T, et al. Synthesis of new tetrazene(N-N N-N)-linked bi(1,2,4- triazole) [J]. Chinese Chemical Letter, 2007, 18: 1176-1178.
    [28]
    Li Y C, Qi C, Li S H, et al. 1,1'-Azobis-1,2,3-triazole: A high-nitrogen compound with stable N 8structure and photochromism [J]. Journal of American Chemical Society, 2010, 132: 12172-12174.
    [29]
    Li Shenghua,, Shi Honggang, Sun Chenghu, et al. Synthesis and crystal structure of 2,2',5,5'-tetrachloro-1,1'-azo-1,3,4-triazole [J]. Chinese Journal of energetic Materials,2009, 1: 7-10. (in Chinese)
    [30]
    Sheldrick D M. SHELXS-97 and SHELXL-97 [M]//Program of Crystal Structure Refinement. Germany: University of Göttingen, 1997.
    [31]
    Li Ming, Wen Lirong, Zhao Guilong, et al. Synthesis and crystal structure of ethyl 5-Amino-1- -3-methylthio-1H-pyrazole-4-carboxylate [J]. Chinese Journal of Structure Chemical, 2005, 24: 74-78. (in Chinese)
    [32]
    Zou Xiajuan, Weng Linhong, Jin Guiyu, et al. Synthesis and crystal structure of N-tert-butyl-N' -(2,4-dichlorobenzoyl-N- hydrazine [J]. Chinese Journal of Structure Chemical, 2001, 20: 344-348. (in Chinese)
    [33]
    Bondi A. Vander waals volumes and radii [J]. Journal of Physical Chemical, 1964, 68: 441-444.
    [34]
    Cady H H, Larson A C. 1-Amino-1-hydrazino-2,2-dinitroethene and corresponding salts: synthesis, characterization, and thermolysis studies [J]. Acta crystallography, 1965, 18: 485-488.
    • Relative Articles
  • Supplements (0)
  • Cited By
  • 加载中

Catalog

    通讯作者:陈斌, bchen63@163.com
    • 1.

      沈阳化工大学材料科学与工程学院 沈阳 110142

    1. 本站搜索
    2. 百度学术搜索
    3. 万方数据库搜索
    4. CNKI搜索
    Get Citation
    PDF
    XML

    Article Metrics

    Article views (1881) PDF downloads(160) Cited by()
    Proportional views
    Related

    Address:5 Zhongguancun South Street, Haidian District, Beijing

    Tel:86-10-68914374

    Email:blgywb@bit.edu.cn

    Copy Right © Journal of Beijing Institute of Technology

    Supported by:Beijing Renhe Information Technology Co. Ltd

    /

      Return
      Return
        Baidu
        map