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]
  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]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  Yuchen Wang , Yaoyu Liu , Xiongfei Huang , Guanjie He , Kai Yan . Fe nanoclusters anchored in biomass waste-derived porous carbon nanosheets for high-performance supercapacitor. Chinese Chemical Letters, 2024, 35(8): 109301-. doi: 10.1016/j.cclet.2023.109301
12. [12]
  Jun Jiang , Tong Guo , Wuxin Bai , Mingliang Liu , Shujun Liu , Zhijie Qi , Jingwen Sun , Shugang Pan , Aleksandr L. Vasiliev , Zhiyuan Ma , Xin Wang , Junwu Zhu , Yongsheng Fu . Modularized sulfur storage achieved by 100% space utilization host for high performance lithium-sulfur batteries. Chinese Chemical Letters, 2024, 35(4): 108565-. doi: 10.1016/j.cclet.2023.108565
13. [13]
  Pingping Wang , Huixian Miao , Kechuan Sheng , Bin Wang , Fan Feng , Xuankun Cai , Wei Huang , Dayu Wu . Efficient blue-light-excitable copper(Ⅰ) coordination network phosphors for high-performance white LEDs. Chinese Chemical Letters, 2024, 35(4): 108600-. doi: 10.1016/j.cclet.2023.108600
14. [14]
  Guiyang Zheng , Xuelian Kang , Haoran Ye , Wei Fan , Christian Sonne , Su Shiung Lam , Rock Keey Liew , Changlei Xia , Yang Shi , Shengbo Ge . Recent advances in functional utilisation of environmentally friendly and recyclable high-performance green biocomposites: A review. Chinese Chemical Letters, 2024, 35(4): 108817-. doi: 10.1016/j.cclet.2023.108817
15. [15]
  Jiayu Bai , Songjie Hu , Lirong Feng , Xinhui Jin , Dong Wang , Kai Zhang , Xiaohui Guo . Manganese vanadium oxide composite as a cathode for high-performance aqueous zinc-ion batteries. Chinese Chemical Letters, 2024, 35(9): 109326-. doi: 10.1016/j.cclet.2023.109326
16. [16]
  Ningning Zhao , Yuyan Liang , Wenjie Huo , Xinyan Zhu , Zhangxing He , Zekun Zhang , Youtuo Zhang , Xianwen Wu , Lei Dai , Jing Zhu , Ling Wang , Qiaobao Zhang . Separator functionalization enables high-performance zinc anode via ion-migration regulation and interfacial engineering. Chinese Chemical Letters, 2024, 35(9): 109332-. doi: 10.1016/j.cclet.2023.109332
17. [17]
  Xiaoxing Ji , Xiaojuan Li , Chenggang Wang , Gang Zhao , Hongxia Bu , Xijin Xu . Ni_xB/rGO as the cathode for high-performance aqueous alkaline zinc-based battery. Chinese Chemical Letters, 2024, 35(10): 109388-. doi: 10.1016/j.cclet.2023.109388
18. [18]
  Xiaotao Jin , Yanlan Wang , Yingping Huang , Di Huang , Xiang Liu . Percarbonate activation catalyzed by nanoblocks of basic copper molybdate for antibiotics degradation: High performance, degradation pathways and mechanism. Chinese Chemical Letters, 2024, 35(10): 109499-. doi: 10.1016/j.cclet.2024.109499
19. [19]
  Jie Zhou , Chuanxiang Zhang , Changchun Hu , Shuo Li , Yuan Liu , Zhu Chen , Song Li , Hui Chen , Rokayya Sami , Yan Deng . Electrochemical aptasensor based on black phosphorus-porous graphene nanocomposites for high-performance detection of Hg²⁺. Chinese Chemical Letters, 2024, 35(11): 109561-. doi: 10.1016/j.cclet.2024.109561
20. [20]
  Wenhao Feng , Chunli Liu , Zheng Liu , Huan Pang . In-situ growth of N-doped graphene-like carbon/MOF nanocomposites for high-performance supercapacitor. Chinese Chemical Letters, 2024, 35(12): 109552-. doi: 10.1016/j.cclet.2024.109552

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(268)
HTML views(3)

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