Citation: Bu-Tong LI, Lu-Lin LI, Chuan YANG. Computational Study of Azide-oxirane as High-energy-density Materials[J]. Chinese Journal of Structural Chemistry, ;2020, 39(7): 1261-1265. doi: 10.14102/j.cnki.0254–5861.2011–2587 shu

Computational Study of Azide-oxirane as High-energy-density Materials

School of Chemistry and Materials Science, Guizhou Education University, Guiyang 550018, China

Corresponding author: Bu-Tong LI, libutong@hotmail.com
Received Date: 29 August 2019
Accepted Date: 1 November 2019

Fund Project: the Natural Science Foundation of Guizhou Education University 14BS017the Natural Science Foundation of Guizhou Province QKHPTRC[2018]5778-09

Figures(1)

The azide oxiranes were studied at the CCSD(T)/cc-PVDZ//MP2/cc-PVDZ level in this paper. The sublimation enthalpies and heats of formation both in gas phase and solid state were calculated. The thermodynamics stability was predicted by using the bond dissociation energy and characteristic height, through which all title compounds are confirmed to be more stable than hexanitrohexaazaisowurtzitane (CL-20) and A, B₁ and D are less sensitive than hexahydro-1, 3, 5, -trinitro-1, 3, 5-triazine (RDX). Furthermore, the detonation property was measured by the specific impulse. The detonation performance of the title compounds is comparable to that of RDX. Our results can provide basic information for the molecular design of novel high-energy-density compounds.
- high-energy-density materials,
- specific impulse,
- isodesmic reactions
1. [1]
  Joo, Y. H.; Shreeve, J. N. M. Nitroimino-tetrazolates and oxy-nitroimino-tetrazolates. J. Am. Chem. Soc. 2010, 132, 15081−15090. doi: 10.1021/ja107729c
2. [2]
  Latypov, N. V.; Bergman, J.; Langlet, A.; Wellmar, U.; Bemm, U. Synthesis and reactions of 1, 1-diamino-2, 2-dinitroethylene. Tetrahedron 1998, 54, 11525−11536. doi: 10.1016/S0040-4020(98)00673-5
3. [3]
  Eaton, P. E.; Gilardi, R. L.; Zhang, M. X. Polynitrocubanes: advanced high-density, high-energy materials. Adv. Mater. 2000, 12, 1143−1148. doi: 10.1002/1521-4095(200008)12:15<1143::AID-ADMA1143>3.0.CO;2-5
4. [4]
  Li, B.; Li, L.; Chen, S. Thermal stability and detonation character of nitro-substituted derivatives of imidazole. J. Mol. Model. 2019, 25, 298−304. doi: 10.1007/s00894-019-4190-5
5. [5]
  Kapur, N.; Ball, D. W. New potential high energy materials: diazocyclopropanes. J. Mol. Struct. Theochem. 2005, 715, 151−155. doi: 10.1016/j.theochem.2004.10.068
6. [6]
  Halstead, J. M.; Whittaker, J. N.; Ball, D. W. Aminonitrocyclopropanes as possible high-energy materials. Quantum chemical calculations. Propellants Explos. Pyrotech. 2012, 37, 498−501. doi: 10.1002/prep.201100102
7. [7]
  Li, B. T.; Li, L. L.; Li, X. Computational study about the derivatives of pyrrole as high-energy-density compounds. Mol. Simul. 2019, 1−6.
8. [8]
  Magers, D. H.; Salter, E. A.; Bartlett, R. J.; Salter, C.; Hess, B. A.; Schaad, L. J. Do stable isomers of N₃H₃ exist? J. Am. Chem. Soc. 1988, 110, 3435−3446. doi: 10.1021/ja00219a016
9. [9]
  Li, B.; Zhou, M.; Peng, J.; Li, L.; Guo, Y. Theoretical calculations about nitro-substituted pyridine as high-energy-density compounds (HEDCs). J. Mol. Model. 2019, 25, 23−28. doi: 10.1007/s00894-018-3904-4
10. [10]
  Enders, D.; Kramps, L.; Zhu, J. Zinc-mediated asymmetric epoxidation of nitro alkenes with oxygen. Tetrahedron: Asymmetry 1998, 9, 3959−3962. doi: 10.1016/S0957-4166(98)00424-8
11. [11]
  Dutkiewicz, M.; Maciejewski, H.; Marciniec, B. Synthesis of azido-, hydroxy- and nitro-, hydroxy-functionalized spherosilicates via oxirane ring-opening reactions. Synthesis 2012, 44, 881−884. doi: 10.1055/s-0031-1289701
12. [12]
  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 Gaussian 03, Revision B. 01 2003.
13. [13]
  Ponomarev, D.; Takhistov, V. What are isodesmic reactions? J. Chem. Educ. 1997, 74, 201−203. doi: 10.1021/ed074p201
14. [14]
  Rice, B. M.; Pai, S. V.; Hare, J. Predicting heats of formation of energetic materials using quantum mechanical calculations. Combust. Flame 1999, 118, 445−458. doi: 10.1016/S0010-2180(99)00008-5
15. [15]
  Fried, L. E.; Manaa, M. R.; Pagoria, P. F.; Simpson, R. L. Design and synthesis of energetic materials. Annu. Rev. Mater. Res. 2001, 31, 291−321. doi: 10.1146/annurev.matsci.31.1.291
16. [16]
  Pospíšil, M.; Vávra, P.; Concha, M.; Murray, J.; Politzer, P. A possible crystal volume factor in the impact sensitivities of some energetic compounds. J. Mol. Model. 2010, 16, 895−901. doi: 10.1007/s00894-009-0587-x
17. [17]
  Parker, V. D.; Handoo, K. L.; Roness, F.; Tilset, M. Electrode potentials and the thermodynamics of isodesmic reactions. J. Am. Chem. Soc. 1991, 113, 7493−7498. doi: 10.1021/ja00020a007
18. [18]
  Li, B.; Chi, W.; Li, L. Theoretical calculation about the high-energy-density molecules of nitrate ester substitution derivatives of prismane. Chin. J. Struct. Chem. 2016, 35, 1306−1312.
19. [19]
  Owens, F. J.; Jayasuriya, K.; Abrahmsen, L.; Politzer, P. Computational analysis of some properties associated with the nitro groups in polynitroaromatic molecules. Chem. Phys. Lett. 1985, 116, 434−438. doi: 10.1016/0009-2614(85)80199-8
20. [20]
  Politzer, P.; Murray, J. S.; Edward, G. M.; Desalvo, M.; Miller, E. Calculation of heats of sublimation and solid phase heats of formation. Mol. Phys. 1997, 91, 923−928. doi: 10.1080/002689797171030
21. [21]
  Mayer, I. Charge, bond order and valence in the ab initio scf theory. Chem. Phys. Lett. 1983, 97, 270−2 doi: 10.1016/0009-2614(83)80005-0
1. [1]
  Xiaoxue Li , Hongwei Zhou , Rongrong Qian , Xu Zhang , Lei Yu . A concise synthesis of Se/Fe materials for catalytic oxidation reactions of anthracene and polyene. Chinese Chemical Letters, 2025, 36(3): 110036-. doi: 10.1016/j.cclet.2024.110036
2. [2]
  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
3. [3]
  Yanhua Peng , Xin Yu , Ting Wang . Adaptive nanoconfined Fenton-like reactions: Tailoring carbon pathways for sustainable water treatment and energy harvesting. Chinese Chemical Letters, 2024, 35(12): 110198-. doi: 10.1016/j.cclet.2024.110198
4. [4]
  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
5. [5]
  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
6. [6]
  Shehla Khalid , Muhammad Bilal , Nasir Rasool , Muhammad Imran . Photochemical reactions as synthetic tool for pharmaceutical industries. Chinese Chemical Letters, 2024, 35(9): 109498-. doi: 10.1016/j.cclet.2024.109498
7. [7]
  Yiming Ma , Yuanbo Wang , Fang Wang , Sheng Lu , Xiaoqiang Chen . Site-specific protein labeling: Recent progress. Chinese Chemical Letters, 2025, 36(8): 110546-. doi: 10.1016/j.cclet.2024.110546
8. [8]
  Feihu Wu , Gengwen Chen , Kaitao Lai , Shiqing Zhang , Yingchao Liu , Ruijian Luo , Xiaocong Wang , Pinzhi Cao , Yi Ye , Jiarong Lian , Junle Qu , Zhigang Yang , Xiaojun Peng . Non-specific/specific SERS spectra concatenation for precise bacteria classifications with few samples using a residual neural network. Chinese Chemical Letters, 2025, 36(1): 109884-. doi: 10.1016/j.cclet.2024.109884
9. [9]
  Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
10. [10]
  Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
11. [11]
  Ying-Di Hao , Zhi-Qian Lin , Xiao-Yu Guo , Jiao Liang , Can-Kun Luo , Qian-Tao Wang , Li Guo , Yong Wu . Rhodium-catalyzed Doyle-Kirmse rearrangement reactions of sulfoxoniun ylides. Chinese Chemical Letters, 2024, 35(4): 108834-. doi: 10.1016/j.cclet.2023.108834
12. [12]
  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
13. [13]
  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
14. [14]
  Xinyu Ren , Hong Liu , Jingang Wang , Jiayuan Yu . Electrospinning-derived functional carbon-based materials for energy conversion and storage. Chinese Chemical Letters, 2024, 35(6): 109282-. doi: 10.1016/j.cclet.2023.109282
15. [15]
  Xiaohong Wen , Mei Yang , Lie Li , Mingmin Huang , Wei Cui , Suping Li , Haiyan Chen , Chen Li , Qiuping Guo . Enzymatically controlled DNA tetrahedron nanoprobes for specific imaging of ATP in tumor. Chinese Chemical Letters, 2024, 35(8): 109291-. doi: 10.1016/j.cclet.2023.109291
16. [16]
  Tianyu Sun , Zhoujun Dong , Paul Michael Malugulu , Tengfei Zhen , Lei Wang , Yao Chen , Haopeng Sun . Advances in design strategies and imaging applications of specific butyrylcholinesterase probes. Chinese Chemical Letters, 2025, 36(7): 110451-. doi: 10.1016/j.cclet.2024.110451
17. [17]
  Renshu Huang , Jinli Chen , Xingfa Chen , Tianqi Yu , Huyi Yu , Kaien Li , Bin Li , Shibin Yin . Synergized oxygen vacancies with Mn2O3@CeO2 heterojunction as high current density catalysts for Li–O2 batteries. Chinese Journal of Structural Chemistry, 2023, 42(11): 100171-100171. doi: 10.1016/j.cjsc.2023.100171
18. [18]
  Chunru Liu , Ligang Feng . Advances in anode catalysts of methanol-assisted water-splitting reactions for hydrogen generation. Chinese Journal of Structural Chemistry, 2023, 42(10): 100136-100136. doi: 10.1016/j.cjsc.2023.100136
19. [19]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
20. [20]
  Shu Lin , Kezhen Qi . Phase-dependent lithium-alloying reactions for lithium-metal batteries. Chinese Chemical Letters, 2024, 35(4): 109431-. doi: 10.1016/j.cclet.2023.109431

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(599)
HTML views(6)

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