Citation: Bu-Tong LI, Lu-Lin LI, Quan-Bao ZHOU. Are the Nitro- and Amino-substituted Piperidine High-energy-density Compounds?[J]. Chinese Journal of Structural Chemistry, ;2020, 39(7): 1266-1270. doi: 10.14102/j.cnki.0254–5861.2011–2619 shu

Are the Nitro- and Amino-substituted Piperidine High-energy-density Compounds?

a.
School of Chemistry and Materials Science, Guizhou Education University, Guiyang 550018, China
b.
Jiangxi Key Laboratory for Mass Spectrometry and Instrumentation, East China University of Technology, Nanchang 330013, China

Corresponding author: Lu-Lin LI, libutong@hotmail.com Quan-Bao ZHOU, quanbao.zhou@outlook.com
Received Date: 25 September 2019
Accepted Date: 13 December 2019

Fund Project: the Natural Science Foundation of Guizhou Education University 14BS017the Natural Science Foundation of Guizhou Education University 2019ZD001the Natural Science Foundation of Guizhou Province QKHPTRC[2018]5778-09

Figures(1)

Nitro and amino groups were introduced into piperidine skeleton to design derivatives of piperidine (labeled as α, β₁, β₂, β₃, γ and δ). Heats of formation (HOFs) are calculated in detail at the B3PW91/6-311+G(d, p) level for these aminonitropiperidines. The results show that all derivatives have negative heats of formation, which were affected by the positions of substituted groups. The molecular stability is estimated and analyzed based on bond dissociation energies (BDE) and characteristic heights (H₅₀). All derivatives designed in this paper are confirmed with lower impact sensitivity than 1, 3, 5-trinitro-1, 3, 5-triazinane (RDX) and 1, 3, 5, 7-tetranitro-1, 3, 5, 7-tetrazocane (HMX). Furthermore, the detonation velocities (D) and the detonation pressures (P) are predicted via the Kamlet-Jacobs equation. In all these molecules, δ has comparable detonation character with that of RDX and HMX and can be the candidate of high-energy-density compounds (HEDCs).
- piperidine derivatives,
- high-energy-density compounds,
- detonation performance
1. [1]
  Murray, J. S.; Concha, M.; Seminario, J. M.; Politzer, P. Computational study of relative bond strengths and stabilities of a series of amine and nitro derivatives of triprismane and some azatriprismanes. J. Phys. Chem. 1991, 95, 1601−1605. doi: 10.1021/j100157a018
2. [2]
  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
3. [3]
  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
4. [4]
  Li, B. T.; Li, L. L.; Li, X. Computational study about the derivatives of pyrrole as high-energy-density compounds. Mol. Simul. 2019, 45, 1459−1464. doi: 10.1080/08927022.2019.1655561
5. [5]
  Liu, T.; Jia, J.; Li, B.; Gao, K. Theoretical exploration on structural stabilities and detonation properties of nitrimino substituted derivatives of cyclopropane. Chin. J. Struct. Chem. 2019, 38, 688−694.
6. [6]
  Tsyshevsky, R.; Pagoria, P.; Zhang, M.; Racoveanu, A.; DeHope, A.; Parrish, D.; Kuklja, M. M. Searching for low-sensitivity cast-melt high-energy-density materials: synthesis, characterization, and decomposition kinetics of 3, 4-bis(4-nitro-1, 2, 5-oxadiazol-3-yl)-1, 2, 5-oxadiazole-2-oxide. J. Phys. Chem. C 2015, 119, 3509−3521. doi: 10.1021/jp5118008
7. [7]
  Agrawal, J. P. Recent trends in high-energy materials. Prog. Energy Combust. Sci. 1998, 24, 1−30. doi: 10.1016/S0360-1285(97)00015-4
8. [8]
  Fischer, D.; Klapötke, T. M.; Stierstorfer, J. 1, 5-di(nitramino) tetrazole: high sensitivity and superior explosive performance. Angew. Chem. Int. Ed. 2015, 54, 10299−10302. doi: 10.1002/anie.201502919
9. [9]
  Boddu, V. M.; Viswanath, D. S.; Ghosh, T. K.; Damavarapu, R. 2, 4, 6-triamino-1, 3, 5-trinitrobenzene (TATB) and TATB-based formulations — a review. J. Hazard. Mater. 2010, 181, 1−8. doi: 10.1016/j.jhazmat.2010.04.120
10. [10]
  Evers, J.; Klapötke, T. M.; Mayer, P.; Oehlinger, G.; Welch, J. α- and β-FOX-7, polymorphs of a high energy density material, studied by X-ray single crystal and powder investigations in the temperature range from 200 to 423 k. Inorg. Chem. 2006, 45, 4996−5007. doi: 10.1021/ic052150m
11. [11]
  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
12. [12]
  Dorohoi, D. O.; Airinei, A.; Dimitriu, M. Intermolecular interactions in solutions of some amino-nitro-benzene derivatives, studied by spectral means. Spectrochim. Acta, Part A 2009, 73, 257−262. doi: 10.1016/j.saa.2009.02.011
13. [13]
  Kofman, T. 5-Amino-3-nitro-1, 2, 4-triazole and its derivatives. Russ. J. Org. Chem. 2002, 38, 1231−1243. doi: 10.1023/A:1021641709157
14. [14]
  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 03, Revision B. 01. Gaussian, Inc., Pittsburgh PA 2003.
15. [15]
  Ponomarev, D.; Takhistov, V. What are isodesmic reactions? J. Chem. Educ. 1997, 74, 201−207. doi: 10.1021/ed074p201
16. [16]
  Kamlet, M. J.; Jacobs, S. J. Chemistry of detonations. I. A simple method for calculating detonation properties of C–H–N–O explosives. J. Chem. Phys. 1968, 48, 23−35. doi: 10.1063/1.1667908
17. [17]
  Kamlet, M. J.; Adolph, H. G. The relationship of impact sensitivity with structure of organic high explosives. Ⅱ. Polynitroaromatic explosives. Propell. Explos. Pyrot. 1979, 4, 30−34. doi: 10.1002/prep.19790040204
18. [18]
  Finch, A.; Gardner, P.; Head, A.; Majdi, H. The enthalpies of formation of 1, 2, 4-triazol-5-one and 3-nitro-1, 2, 4-triazol-5-one. J. Chem. Thermodyn. 1991, 23, 1169−1173. doi: 10.1016/S0021-9614(05)80150-8
19. [19]
  Lenchitz, C.; Velicky, R.; Silvestr, G.; Schlosbe, L. P. Thermodynamic properties of several nitrotoluenes. J. Chem. Thermodyn. 1971, 3, 689−712. doi: 10.1016/S0021-9614(71)80090-3
20. [20]
  Harper, L. K.; Shoaf, A. L.; Bayse, C. A. Predicting trigger bonds in explosive materials through wiberg bond index analysis. ChemPhysChem. 2015, 16, 3886−3892. doi: 10.1002/cphc.201500773
1. [1]
  Wei Sun , Anjing Liao , Li Lei , Xu Tang , Ya Wang , Jian Wu . Research progress on piperidine-containing compounds as agrochemicals. Chinese Chemical Letters, 2025, 36(1): 109855-. doi: 10.1016/j.cclet.2024.109855
2. [2]
  Malaika Arshad , Zia Ul Haq Khan , Swera Talib , Sana Sabahat , Noor Samad Shah , Huma Ajab , Farooq Ahmad , Syed Khasim , M. A. Diab , Heba A. El-Sabban . A comprehensive review: MOFs and their derivatives as high-performance supercapacitor electrodes. Chinese Journal of Structural Chemistry, 2025, 44(9): 100676-100676. doi: 10.1016/j.cjsc.2025.100676
3. [3]
  Kun Zhang , Li-Min Zhao , Tianhao Xing , Yueyue Bu , Qingyun Wang , Christophe Pannecouque , Erik De Clercq , Angela Corona , Laura Dettori , Enzo Tramontano , Shuai Wang , Fen-Er Chen . Rational structure-based design and optimization of next-generation biphenyl-piperidine-triazine derivatives as potent non-nucleoside reverse transcriptase inhibitors. Chinese Chemical Letters, 2026, 37(1): 111283-. doi: 10.1016/j.cclet.2025.111283
4. [4]
  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
5. [5]
  Sheng Tang , Mingyue Liao , Weihai Sun , Jihuai Wu , Jiamin Lu , Yiming Xie . Optimizing CsPbBr₃ perovskite solar cell interface and performance through tetraphenylethene derivatives. Chinese Chemical Letters, 2025, 36(6): 110838-. doi: 10.1016/j.cclet.2025.110838
6. [6]
  Hao Liu , Pin Zhao , Yao Jiang , Subo Xu , Weilong Song , Xinhua Wang . Influence of the interlayer properties on the thin-film composite membrane performance based on UiO-66 and its derivatives. Chinese Chemical Letters, 2026, 37(5): 111862-. doi: 10.1016/j.cclet.2025.111862
7. [7]
  Ruilong WANG , Jinlong MAO , Guoxia JIN , Jianping MA , Haiying WANG , Jie QIN . 2-Cyanobenzyl-substituted [FeFe]-hydrogenase compounds: Preparation, characterization, and photocatalytic H₂-production performance. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 817-825. doi: 10.11862/CJIC.20250376
8. [8]
  Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
9. [9]
  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
10. [10]
  Mengya Ge , Zijie Zhou , Huaiyang Zhu , Ying Wang , Chao Wang , Chao Lai , Qinghong Wang . Multifunctional gel electrolytes for high-performance zinc metal batteries. Chinese Chemical Letters, 2025, 36(7): 110121-. doi: 10.1016/j.cclet.2024.110121
11. [11]
  Xiaoqian Wei , Hanyu Gao , Tiantian Wang , Zijian Li , Yanru Geng , Guiping Zheng , Min Gyu Kim , Haeseong Jang , Xien Liu , Qing Qin . Neodymium-doped hollow Ir/IrO2 nanospheres with low geometric iridium density enable excellent acidic water oxidation performance. Chinese Journal of Structural Chemistry, 2025, 44(7): 100600-100600. doi: 10.1016/j.cjsc.2025.100600
12. [12]
  Kai Guo , Jiating Li , Shiya Lin , Lu Chen , Neng Yu , Yiju Li . Dual-function additive for simultaneously boosting the stability and energy density of aqueous zinc ion hybrid capacitors. Chinese Chemical Letters, 2026, 37(4): 111175-. doi: 10.1016/j.cclet.2025.111175
13. [13]
  Wen LUO , Lin JIN , Palanisamy Kannan , Jinle HOU , Peng HUO , Jinzhong YAO , Peng WANG . Preparation of high-performance supercapacitor based on bimetallic high nuclearity titanium-oxo-cluster based electrodes. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 782-790. doi: 10.11862/CJIC.20230418
14. [14]
  Zhe Wang , Li-Peng Hou , Qian-Kui Zhang , Nan Yao , Aibing Chen , Jia-Qi Huang , Xue-Qiang Zhang . High-performance localized high-concentration electrolytes by diluent design for long-cycling lithium metal batteries. Chinese Chemical Letters, 2024, 35(4): 108570-. doi: 10.1016/j.cclet.2023.108570
15. [15]
  Haokun Yuan , Anjing Liao , Shunhong Chen , Yiming Tian , Yaming Liu , Jian Wu . Pyrimidine derivatives in discovery of pesticides: A review. Chinese Chemical Letters, 2026, 37(2): 111305-. doi: 10.1016/j.cclet.2025.111305
16. [16]
  Jian Wang , Baohui Wang , Pin Ma , Yifei Zhang , Honghong Gong , Biyun Peng , Sen Liang , Yunchuan Xie , Hailong Wang . Regulation of uniformity and electric field distribution achieved highly energy storage performance in PVDF-based nanocomposites via continuous gradient structure. Chinese Chemical Letters, 2025, 36(4): 109714-. doi: 10.1016/j.cclet.2024.109714
17. [17]
  You-Song Ding , Qing-Song Yang , Zhiping Zheng . Pentavalent praseodymium complexes culminated in the pursuit of high-valence lanthanide compounds. Chinese Journal of Structural Chemistry, 2025, 44(11): 100696-100696. doi: 10.1016/j.cjsc.2025.100696
18. [18]
  Xinyu Huai , Jingxuan Liu , Xiang Wu . Cobalt-Doped NiMoO4 Nanosheet for High-performance Flexible Supercapacitor. Chinese Journal of Structural Chemistry, 2023, 42(10): 100158-100158. doi: 10.1016/j.cjsc.2023.100158
19. [19]
  Fangzhou Wang , Wentong Gao , Chenghui Li . A weak but inert hindered urethane bond for high-performance dynamic polyurethane polymers. Chinese Chemical Letters, 2024, 35(5): 109305-. doi: 10.1016/j.cclet.2023.109305
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1213)
HTML views(31)

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