Citation: Ke-Hui Hou, Cong-Ming Ma, Zu-Liang Liu. Synthesis, characterization and theoretical study of 2-azido-4-nitroimidazole-based energetic salts[J]. Chinese Chemical Letters, ;2014, 25(3): 438-440. doi: 10.1016/j.cclet.2013.12.007 shu

Synthesis, characterization and theoretical study of 2-azido-4-nitroimidazole-based energetic salts

1.
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China

Corresponding author: Zu-Liang Liu,
Received Date: 28 August 2013
Available Online: 27 November 2013

The 2-azido-4-nitroimidazole-based energetic salts were synthesized in a simple and straightforward manner. The structures of these new salts were determined by IR, ¹H NMR and ¹³C NMR spectroscopy and elemental analysis. These salts also exhibited high positive enthalpies of formation, high nitrogen content, and moderate detonation properties.
- Synthesis,
- Energetic compounds,
- Heats of formation,
- 2-Azido-4-nitroimidazole
1. [1]
  [1] (a) R.P. Singh, R.D. Verma, D.T. Meshri, J.M. Shreeve, Energetic nitrogen-rich salts and ionic liquids, Angew. Chem. Int. Ed. 45 (2006) 3584-3601; (b) H. Gao, C. Ye, O.D. Gupta, et al., 2,4,5-Trinitroimidazole-based energetic salts, Chem. Eur. J. 13 (2007) 3853-3860; (c) R. Duddu, P.R. Dave, R. Damavarapu, N. Gelber, D. Parrish, Synthesis of Namino-and N-nitramino-nitroimidazoles, Tetrahedron Lett. 51 (2010) 399-401; (d) R. Duddu, M.X. Zhang, R. Damavarapu, N. Gelber, Molten-state nitration of substituted imidazoles: new synthetic approaches to the novel melt-cast energetic material, 1-methyl-2,4,5-trinitroimidazole, Synthesis 17 (2011) 2864-2895.
2. [2]
  [2] D. Srinivas, V.D. Ghule, K. Muralidharan, H.D.B. Jenkins, Tetraanionic nitrogen-rich tetrazole-based energetic salts, Chem. Asian J. 8 (2013) 1023-1028.
3. [3]
  [3] J.H. Zhang, C.L. He, D.A. Parrish, J.M. Shreeve, Nitramines with varying sensitivities: functionalized dipyrazolyl-N-nitromethanamines as energetic materials, Chem. Eur. J. 19 (2013) 8929-8936.
4. [4]
  [4] A. Hammerl, T.M. Klapötke, Tetrazolylpentazoles: nitrogen-rich compounds, Inorg. Chem. 41 (2002) 906-912.
5. [5]
  [5] Z. Tang, L. Yang, X.J. Qiao, et al., Crystal structure, thermal decomposition and sensitivity properties of (AIM)(HTNR) and (AIM)(PA), Chem. Res. Chin. Univ. 28 (2012) 4-8.
6. [6]
  [6] Z. Tang, L. Yang, X.J. Qiao, et al., Crystal structure and thermal analysis of two new energetic compounds (AIM)NO₃ and (AIM)(HTNR) H₂O, Acta Chim. Sin. 70 (2012) 471-478.
7. [7]
  [7] M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 09, Gaussian, Inc., Wallingford, CT, 2009.
8. [8]
  [8] W.J. Hehre, R. Ditchfield, J.A. Pople, Self-consistent molecular orbital methods. XⅡ. Further extensions of Gaussian-type basis sets for use in molecular orbital studies of organic molecules, J. Chem. Phys. 56 (1972) 2257-2261.
9. [9]
  [9] (a) H.D.B. Jenkins, Thermodynamics of the relationship between lattice energy and lattice enthalpy, J. Chem. Educ. 82 (2005) 950-952; (b) H.D.B. Jenkins, D. Tudela, L. Glasser, Lattice potential energy estimation for complex ionic salts from density measurements, Inorg. Chem. 41 (2002) 2364-2367; (c) L. Glasser, H.D.B. Jenkins, Lattice energies and unit cell volumes of complex ionic solids, J. Am. Chem. Soc. 122 (2000) 632-638; (d) H.D.B. Jenkins, H.K. Roobottom, J. Passmore, L. Glasser, Relationships among ionic lattice energies, molecular (formula unit) volumes, and thermochemical radii, Inorg. Chem. 38 (1999) 3609-3620.
10. [10]
  [10] D.W.M. Hofmann, Fast estimation of crystal densities, Acta Crystallogr. B 58 (2002) 489-493.
11. [11]
  [11] (a) M.J. Kamlet, S.J. Jacobs, Chemistry of detonations. I. A simple method for calculating detonation properties of C-H-N-O explosives, J. Chem. Phys. 48 (1968) 23-25; (b) M.J. Kamlet, J.E. Ablard, Chemistry of detonations. Ⅱ. Buffered equilibria, J. Chem. Phys. 48 (1968) 36-42.
1. [1]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
2. [2]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
3. [3]
  Mei Peng , Wei-Min He . Photochemical synthesis and group transfer reactions of azoxy compounds. Chinese Chemical Letters, 2024, 35(8): 109899-. doi: 10.1016/j.cclet.2024.109899
4. [4]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
5. [5]
  Genxiang Wang , Linfeng Fan , Peng Wang , Junfeng Wang , Fen Qiao , Zhenhai Wen . Efficient synthesis of nano high-entropy compounds for advanced oxygen evolution reaction. Chinese Chemical Letters, 2025, 36(4): 110498-. doi: 10.1016/j.cclet.2024.110498
6. [6]
  Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
7. [7]
  Liyong Ding , Zhenhua Pan , Qian Wang . 2D photocatalysts for hydrogen peroxide synthesis. Chinese Chemical Letters, 2024, 35(12): 110125-. doi: 10.1016/j.cclet.2024.110125
8. [8]
  Yin-Hang Chai , Li-Long Dang . New structural breakthrough and topological transformation of homogeneous metalla[4]catenane compounds. Chinese Journal of Structural Chemistry, 2024, 43(10): 100322-100322. doi: 10.1016/j.cjsc.2024.100322
9. [9]
  Ying Li , Long-Jie Wang , Yong-Kang Zhou , Jun Liang , Bin Xiao , Ji-Shen Zheng . An improved installation of 2-hydroxy-4-methoxybenzyl (iHmb) method for chemical protein synthesis. Chinese Chemical Letters, 2024, 35(5): 109033-. doi: 10.1016/j.cclet.2023.109033
10. [10]
  Zhixiang Li , Zhirong Yang , Chang Yao , Bin Wu , Gang Qian , Xuezhi Duan , Xinggui Zhou , Jing Zhang . Efficient continuous synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole in a millimeter scale photoreactor. Chinese Chemical Letters, 2024, 35(4): 108893-. doi: 10.1016/j.cclet.2023.108893
11. [11]
  Juanjuan Wang , Fang Wang , Bin Qin , Yue Wu , Huan Yang , Xiaolong Li , Lanfang Wang , Xiufang Qin , Xiaohong Xu . Controlled synthesis and excellent magnetism of ferrimagnetic NiFe₂Se₄ nanostructures. Chinese Chemical Letters, 2024, 35(11): 109449-. doi: 10.1016/j.cclet.2023.109449
12. [12]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
13. [13]
  Yubang Li , Xixi Hu , Daiqian Xie . The microscopic formation mechanism of O + H2 products from photodissociation of H2O. Chinese Journal of Structural Chemistry, 2024, 43(5): 100274-100274. doi: 10.1016/j.cjsc.2024.100274
14. [14]
  Hui Li , Yanxing Qi , Jia Chen , Juanjuan Wang , Min Yang , Hongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO₂ and selectivity over N₂ and CH₄. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659
15. [15]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
16. [16]
  Ruofan Yin , Zhaoxin Guo , Rui Liu , Xian-Sen Tao . Ultrafast synthesis of Na₃V₂(PO₄)₃ cathode for high performance sodium-ion batteries. Chinese Chemical Letters, 2025, 36(2): 109643-. doi: 10.1016/j.cclet.2024.109643
17. [17]
  Hongjin Shi , Guoyin Yin , Xi Lu , Yangyang Li . Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals. Chinese Chemical Letters, 2024, 35(12): 109674-. doi: 10.1016/j.cclet.2024.109674
18. [18]
  Ya-Nan Yang , Zi-Sheng Li , Sourav Mondal , Lei Qiao , Cui-Cui Wang , Wen-Juan Tian , Zhong-Ming Sun , John E. McGrady . Metal-metal bonds in Zintl clusters: Synthesis, structure and bonding in [Fe₂Sn₄Bi₈]^3– and [Cr₂Sb₁₂]^3–. Chinese Chemical Letters, 2024, 35(8): 109048-. doi: 10.1016/j.cclet.2023.109048
19. [19]
  Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
20. [20]
  Xiangjun Zhang , Xiaodi Yang , Yan Wang , Zhongping Xu , Sisi Yi , Tao Guo , Yue Liao , Xiyu Tang , Jianxiang Zhang , Ruibing Wang . A supramolecular nanoprodrug for prevention of gallstone formation. Chinese Chemical Letters, 2025, 36(2): 109854-. doi: 10.1016/j.cclet.2024.109854

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(556)
HTML views(2)

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