Citation: MEI Zheng, LI Xiao-Hong, CUI Hong-Ling, WANG Hui-Xian, ZHANG Rui-Zhou. Theoretical Studies on the Structure and Detonation Properties of a Furazan-based Energetic Macrocycle Compound[J]. Chinese Journal of Structural Chemistry, ;2016, 35(1): 16-24. doi: 10.14102/j.cnki.0254-5861.2011-0602 shu

Theoretical Studies on the Structure and Detonation Properties of a Furazan-based Energetic Macrocycle Compound

1.
College of Physics and Engineering, Henan University of Science and Technology, Luoyang 471003, China

Received Date: 9 October 2015
Available Online: 13 December 2015
Fund Project: This project was supported by the National Natural Science Foundation of China (No. U1304111) (No. U1304111)the Innovation Team of Henan University of Science and Technology (2015XTD001) (No. 14HASTIT039)

Based on the full optimized molecular geometric structure at 6-311++G** level, the density (ρ), detonation velocity (D), and detonation pressure (P) for a new furazan-based energetic macrocycle compound, hexakis[1,2,5]oxadi-azole[3,4-c:3',4'-e;3'',4''-g:3''',4'''-k:3'''',4''''-m:3''''', 4'''''-o][1,2,9,10]-tetraazacyclohexadecine, were investigated to verify its capacity as high energy density material (HEDM). The infrared spectrum was also predicted. The heat of formation (HOF) was calculated using designed isodesmic reaction. The calculation on the bond dissociation energies (BDEs) was done and the pyrolysis mechanism of the compound was studied. The result shows that the N₃-O₁ bond in the ring may be the weakest one and the ring cleavage is possible to happen in thermal decomposition. The condensed phase HOF and the crystal density were also calculated for the title compound. The detonation data show that it can be considered as a potential HEDM. These results would provide basic information for the molecular design of novel high energy materials.
- detonation properties,
- heat of formation,
- high energy density material,
- isodesmic reaction
1. [1]
  (1) Benson, F. R. The High Nitrogen Compounds. Wiley-Interscience: New York 1984, p120-122.
2. [2]
  (2) Sikder, A. K.; Sikder, N. A review of advanced high performance, insensitive and thermally stable energetic materials emerging for military and space applications. J. Hazard. Mater. 2004, 112, 1-15.
3. [3]
  (3) Hiskey, M.; Goldman, N. High-nitrogen energetic materials derived from azotetrazolate. Energ. Mater. 1998, 16, 119-127.
4. [4]
  (4) Zelenin, A. K.; Trudell, M. L. Synthesis and structure of dinitroazofurazan. J. Heterocycl. Chem. 1998, 35, 151-155.
5. [5]
  (5) Millar, R. W.; Philbin, S. P.; Claridge, R. P.; Hamid, J. Studies of novel heterocyclic insensitive fligh explosive compounds: pyridines, pyrimidines, pyrazines and their bicyclic analogues. Propellant Explos. Pyrotech. 2004, 29, 81-92.
6. [6]
  (6) Chapman, R. D.; Wilson, W. S.; Fronabarger, J. W.; Merwin, L. H.; Ostrom, G. S. Prospects of fused polycyclic nitroazines as thermally insensitive energetic materials. Thermochim. Acta 2002, 384, 229-243.
7. [7]
  (7) Politzer, P.; Pat, L.; Murray, J. S. Computational characterization of a potential energetic compound: 1,3,5,7-tetranitro-2,4,6,8-tetraazacubane. Cen. Eur. J. Energet. Mater. 2011, 8, 39-52.
8. [8]
  (8) Nielsen, A. T. Polycyclic Amine Chemistry, in: Chemistry of Energetic Materials. Academic Press: San Diego 1991, p253-254.
9. [9]
  (9) David, E.; Chavez, D. A.; Parrish, P. L. The synthesis and characterization of a new furazan heterocyclic system. Synlett. 2012, 23, 2126-2128.
10. [10]
  (10) Kohn, W.; Sham, L. J. Self-consistent equations including exchange and correlation effects. Phys. Rev. 1965, 140, A1133-A1138.
11. [11]
  (11) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh PA 2003, Gaussian 03, Revision B. 02.
12. [12]
  (12) Li, X. H.; Cheng, Q. D.; Zhang, X. Z. Density functional theory study of several nitrotriazole derivatives. J. Energet. Mater. 2010, 28, 251-272.
13. [13]
  (13) Kamlet, M. J.; Jacobs, S. J. A simple method for calculating detonation properties of C,H,N,O explosives. J. Chem. Phys. 1968, 48, 23-35.
14. [14]
  (14) Atkins, P. W. Physical Chemistry. Oxford University Press: Oxford 1982, p247-249.
15. [15]
  (15) Politzer, P.; Pat, L.; Murray, J. S. Computational characterization of two di-1,2,3,4-tetrazine tetraoxides, DTTO and iso-DTTO,
16. [16]
  as potential energetic compounds. Cen. Eur. J. Energet. Mater. 2013, 10, 37-52.
17. [17]
  (16) Byrd, E. F. C.; Rice, B. M. Improved prediction of heats of formation of energetic materials using quantum chemical calculations. J. Phys. Chem. A 2006, 10, 1005-1013.
18. [18]
  (17) Lu, T.; Chen, F. W. Multiwfn: a multifunctional wavefunction analyzer. J. Comp. Chem. 2012, 33, 580-592.
19. [19]
  (18) Qiu, L.; Xiao, H.; Gong, X.; Ju, X.; Zhu, W. Crystal density predictions for nitramines based on quantum chemistry. J. Hazard. Mater. 2007, 141, 280-288.
20. [20]
  (19) Frank, H. A.; Olga, K.; David, G. W. Table of bond lengths determined by X-ray and neutron diffraction. J. Chem. Soc. Perkin Trans. II 1987, 12, S1-S19.
21. [21]
  (20) Batog, L. V.; Konstantinova, L. S.; Eman, V. E.; Sukhanov, M. S.; Batsanov, A. S.; Struchkov, Y. T.; Lebedev, O. V.; Khmel'nitskii, L. I. Novel method for synthesis of 3,4:7,8:11,12:15,16-tetrafurazano-1,2,5,6,9,10,13,14-octaazacyclohexadeka-1,3,5,7,9,11,13,15-octaene and its crystal structure. Chem. Heterocy. Comp. 1996, 32, 352-354.
22. [22]
  (21) Lide, D. R. Handbook of Chemistry and Physics. 84th ed. CRC Press LLC: Boca Raton 2004, 108-121.
23. [23]
  (22) Talawar, M. B.; Sivabalan, R.; Mukundan, T.; Muthurajan, H.; Sikder, A. K.; Gandhe, B. R.; Rao, A. S. Environmentally compatible next generation green energetic materials (GEMs). J. Hazard. Mater. 2009, 161, 589-607.
24. [24]
  (23) Hobbs, M. L.; Baer, M. R. Calibration of the BKW-EOS with a large product species data base and measured C-J properties, in: proceedings of the 10th symposium (international) on detonation, ONR 33395-12, Boston, MA, 12-16 July. 1993, p409-418.
25. [25]
  (24) Xiao, H. M.; Chen, Z. X. The Modern Theory for Tetrazole Chemistry. Science Press: Beijing 2000, p153-154.
26. [26]
  (25) Zhang, X. W.; Zhu, W. H.; Xiao, H. M. Comparative theoretical studies of energetic substituted carbon- and nitrogen-bridged difurazans. J. Phys. Chem. A 2010, 114, 603-612.
1. [1]
  Qingyun Hu , Wei Wang , Junyuan Lu , He Zhu , Qi Liu , Yang Ren , Hong Wang , Jian Hui . High-throughput screening of high energy density LiMn_1-xFe_xPO₄ via active learning. Chinese Chemical Letters, 2025, 36(2): 110344-. doi: 10.1016/j.cclet.2024.110344
2. [2]
  Rui Wang , Yuan Tian , Xuefeng Gao , Lei Jiang . Design and fabrication of triangle-pattern superwettability hybrid surface with high-efficiency condensation heat transfer performance. Chinese Chemical Letters, 2025, 36(3): 110395-. doi: 10.1016/j.cclet.2024.110395
3. [3]
  Weibin Shen , Jie Liu , Gongyu Wen , Shuai Li , Binhui Yu , Shuangyu Song , Bojie Gong , Rongyang Zhang , Shibao Liu , Hongpeng Wang , Yao Wang , Yujing Liu , Huadong Yuan , Jianming Luo , Shihui Zou , Xinyong Tao , Jianwei Nai . Formation of FeNi-based nanowire-assembled superstructures with tunable anions for electrocatalytic oxygen evolution reaction. Chinese Chemical Letters, 2025, 36(7): 110184-. doi: 10.1016/j.cclet.2024.110184
4. [4]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
5. [5]
  Zhao Li , Huimin Yang , Wenjing Cheng , Lin Tian . Recent progress of in situ/operando characterization techniques for electrocatalytic energy conversion reaction. Chinese Chemical Letters, 2024, 35(9): 109237-. doi: 10.1016/j.cclet.2023.109237
6. [6]
  Zhengkun QIN , Zicong PAN , Hui TIAN , Wanyi ZHANG , Mingxing SONG . A series of iridium(Ⅲ) complexes with fluorophenyl isoquinoline ligand and low-efficiency roll-off properties: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1235-1244. doi: 10.11862/CJIC.20240429
7. [7]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
8. [8]
  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
9. [9]
  Shunshun Jiang , Ji Zhang , Jing Wang , Shan-Tao Zhang . Excellent energy storage properties in non-stoichiometric Bi_0.5Na_0.5TiO₃-based relaxor ferroelectric ceramics. Chinese Chemical Letters, 2024, 35(7): 108955-. doi: 10.1016/j.cclet.2023.108955
10. [10]
  Kunsong Hu , Yulong Zhang , Jiayi Zhu , Jinhua Mai , Gang Liu , Manoj Krishna Sugumar , Xinhua Liu , Feng Zhan , Rui Tan . Nano-engineered catalysts for high-performance oxygen reduction reaction. Chinese Chemical Letters, 2024, 35(10): 109423-. doi: 10.1016/j.cclet.2023.109423
11. [11]
  Hongyu Tang , Dongming Liu , Jinfu Huang , Liang Zhang , Yang Tang , Bin Huang , Yanwei Li , Shunhua Xiao , Yiling Sun , Renheng Wang . Excellent structural stability and electrochemical properties of LiNi_0.9Co_0.05Mn_0.05O₂ material by surface Ni²⁺ anchoring and Cs⁺ doping. Chinese Chemical Letters, 2025, 36(6): 109987-. doi: 10.1016/j.cclet.2024.109987
12. [12]
  Fenglin Wang , Chengwei Kuang , Zhicheng Zheng , Dan Wu , Hao Wan , Gen Chen , Ning Zhang , Xiaohe Liu , Renzhi Ma . Noble metal clusters substitution in porous Ni substrate renders high mass-specific activities toward oxygen evolution reaction and methanol oxidation reaction. Chinese Chemical Letters, 2025, 36(6): 109989-. doi: 10.1016/j.cclet.2024.109989
13. [13]
  Yunfei Shen , Long Chen . Gradient imprinted Zn metal anodes assist dendrites-free at high current density/capacity. Chinese Journal of Structural Chemistry, 2024, 43(10): 100321-100321. doi: 10.1016/j.cjsc.2024.100321
14. [14]
  Zhilong Xie , Guohui Zhang , Ya Meng , Yefei Tong , Jian Deng , Honghui Li , Qingqing Ma , Shisong Han , Wenjun Ni . A natural nano-platform: Advances in drug delivery system with recombinant high-density lipoprotein. Chinese Chemical Letters, 2024, 35(11): 109584-. doi: 10.1016/j.cclet.2024.109584
15. [15]
  Baokang Geng , Xiang Chu , Li Liu , Lingling Zhang , Shuaishuai Zhang , Xiao Wang , Shuyan Song , Hongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924
16. [16]
  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
17. [17]
  Kun Zhang , Ni Dan , Dan-Dan Ren , Ruo-Yu Zhang , Xiaoyan Lu , Ya-Pan Wu , Li-Lei Zhang , Hong-Ru Fu , Dong-Sheng Li . A small D-A molecule with highly heat-resisting room temperature phosphorescence for white emission and anti-counterfeiting. Chinese Journal of Structural Chemistry, 2024, 43(3): 100244-100244. doi: 10.1016/j.cjsc.2024.100244
18. [18]
  Tingting Liu , Pengfei Sun , Wei Zhao , Yingshuang Li , Lujun Cheng , Jiahai Fan , Xiaohui Bi , Xiaoping Dong . Magnesium doping to improve the light to heat conversion of OMS-2 for formaldehyde oxidation under visible light irradiation. Chinese Chemical Letters, 2024, 35(4): 108813-. doi: 10.1016/j.cclet.2023.108813
19. [19]
  Yu ZHANG , Fangfang ZHAO , Cong PAN , Peng WANG , Liangming WEI . Application of double-side modified separator with hollow carbon material in high-performance Li-S battery. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1218-1232. doi: 10.11862/CJIC.20230412
20. [20]
  Zhiqing Ge , Zuxiong Pan , Shuo Yan , Baoying Zhang , Xiangyu Shen , Mozhen Wang , Xuewu Ge . Novel high-temperature thermochromic polydiacetylene material and its application as thermal indicator. Chinese Chemical Letters, 2024, 35(11): 109850-. doi: 10.1016/j.cclet.2024.109850

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(2559)
HTML views(21)

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