Citation: Bu-Tong LI, Lu-Lin LI, Chuan YANG. Theoretical Study on Nitroso-Substituted Derivatives of Azetidine as Potential High Energy Density Compounds[J]. Chinese Journal of Structural Chemistry, ;2020, 39(4): 643-650. doi: 10.14102/j.cnki.0254-5861.2011-2501 shu

Theoretical Study on Nitroso-Substituted Derivatives of Azetidine as Potential High Energy Density Compounds

School of Chemistry and Materials Science, Guizhou Education University, Guiyang 051008, China

Corresponding author: Bu-Tong LI, libutong@hotmail.com
Received Date: 17 June 2019
Accepted Date: 11 September 2019

Fund Project: the Natural Science Foundation of Guizhou Province QKHPTRC[2018]5778-09the Natural Science Foundation of Guizhou Province QKHJC[2020]1Y038the Natural Science Foundation of Guizhou Education University 14BS017the Natural Science Foundation of Guizhou Education University 2019ZD001

Figures(1)

At the B3PW91/6-311+G(d,p)//MP2/6-311+G(d,p) level, molecular densities, detonation velocities, and detonation pressures of nitroso substituted derivatives of azetidine with their thermal stabilities were investigated to look for high energy density compounds (HEDCs). It was found that the azetidine derivatives had high heat of formation (HOF) and large bond dissociation energy (BDE). Intramolecular hydrogen bonds were located in three molecules (1, 4, and 5), and the molecular stability were improved markedly as well. For 5 and 6, the detonation performances (D= 9.36km/s and 10.80km/s, P= 44.42GPa and 60.70GPa, respectively) meet requirements as high energy density compounds. This work may provide basic information for further study of title compounds.
- high energy density compounds,
- Kamlet-Jacobs equation,
- azetidine derivatives
1. [1]
  Huynh M. H. V.; Hiskey M. A.; Chavez D. E.; Naud D. L.; Gilardi R. D. Synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C−N Compound. J. Am. Chem. Soc. 2005, 127, 12537−12543. doi: 10.1021/ja0509735
2. [2]
  Gutowski K. E.; Rogers R. D.; Dixon D. A. Accurate Thermochemical properties for energetic materials applications. Ⅱ. Heats of formation of imidazolium-, 1,2,4-Triazolium-, and tetrazolium-based energetic salts from isodesmic and lattice energy calculations. J. Phys. Chem. B 2007, 111, 4788−4800. doi: 10.1021/jp066420d
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]
  Shu X.; Tian Y.; Song G.; Zhang H.; Kang B.; Zhang C.; Liu Y.; Liu X.; Sun J. Thermal expansion and theoretical density of 2, 2′, 4, 4′, 6, 6′-hexanitrostilbene. J. Mater. Sci. 2011, 46, 2536−2540. doi: 10.1007/s10853-010-5105-0
5. [5]
  Li Y.; Feng X.; Liu H.; Hao J.; Redfern S. A. T.; Lei W.; Liu D.; Ma Y. Route to high-energy density polymeric nitrogen t-N via He-N compounds. Nat. Commun. 2018, 9, 722−728. doi: 10.1038/s41467-018-03200-4
6. [6]
  Wu J.; Huang Y.; Yang L.; Geng D.; Wang F.; Wang H.; Chen L. Reactive molecular dynamics simulations of the thermal decomposition mechanism of 1,3,3-trinitroazetidine (TNAZ). ChemPhysChem 2018, 19, 2683−2695. doi: 10.1002/cphc.201800550
7. [7]
  Liu F. L.; Liu Y.; Zhang L.; Wu Y. M. A dodecahedrane-like molecule C₁₂H₁₂B₈ with uncommon T_h symmetry. Chinese J. Struct. Chem. 2012, 31, 677−682.
8. [8]
  Mei Z.; Li X. H.; Cui H. L.; Wang H. X.; Zhang R. Z. Theoretical studies on the structure and detonation properties of a furazan- based energetic macrocycle compound. Chinese J. Struct. Chem. 2016, 35, 16−24.
9. [9]
  Smith G. D.; Bharadwaj R. K. Quantum chemistry based force field for simulations of HMX. J. Phys. Chem. B 1999, 103, 3570−3575. doi: 10.1021/jp984599p
10. [10]
  Brill T. B.; Gongwer P. E.; Williams G. K. Thermal decomposition of energetic materials. 66. kinetic compensation effects in HMX, RDX, and NTO. J. Phys. Chem. 1994, 98, 12242−12247. doi: 10.1021/j100098a020
11. [11]
  Alavi G.; Chung M.; Lichwa J.; D'Alessio M.; Ray C. The fate and transport of RDX, HMX, TNT and DNT in the volcanic soils of Hawaii: A laboratory and modeling study. J. Hazard. Mater. 2011, 185, 1600−1604. doi: 10.1016/j.jhazmat.2010.10.039
12. [12]
  Ariyarathna T.; Ballentine M.; Vlahos P.; Smith R. W.; Cooper C.; Bohlke J. K.; Fallis S.; Groshens T. J.; Tobias C. Tracing the cycling and fate of the munition, Hexahydro-1,3,5-trinitro-1,3,5-triazine in a simulated sandy coastal marine habitat with a stable isotopic tracer, (15)N-[RDX]. Sci. Total. Environ. 2019, 647, 369−378. doi: 10.1016/j.scitotenv.2018.07.404
13. [13]
  Eberly J. O.; Mayo M. L.; Carr M. R.; Crocker F. H.; Indest K. J. Detection of hexahydro-1,3-5-trinitro-1,3,5-triazine (RDX) with a microbial sensor. J. Gen. Appl. Microbiol. 2019, 64, 139−144.
14. [14]
  Archibald T. G.; Gilardi R.; Baum K.; George C. Synthesis and x-ray crystal structure of 1,3,3-trinitroazetidine. J. Org. Chem. 1990, 55, 2920−2924. doi: 10.1021/jo00296a066
15. [15]
  Thompson C. A.; Rice J. K.; Russell T. P.; Seminario J. M.; Politzer P. Vibrational analysis of 1,3,3-trinitroazetidine using matrix isolation infrared spectroscopy and quantum chemical calculations. J. Phys. Chem. A 1997, 101, 7742−7748. doi: 10.1021/jp971173m
16. [16]
  Sikder N.; Sikder A. K.; Bulakh N. R.; Gandhe B. R. 1,3,3-Trinitroazetidine (TNAZ), a melt-cast explosive: synthesis, characterization and thermal behaviour. J. Hazard. Mater. 2004, 113, 35−43. doi: 10.1016/j.jhazmat.2004.06.002
17. [17]
  Hammerl A.; Klapötke T. M.; Nöth H.; Warchhold M.; Holl G.; Kaiser M.; Ticmanis U. [N₂H₅]⁺²[N₄C−NN−CN₄]^2-: A new high-nitrogen high-energetic material. Inorg. Chem. 2001, 40, 3570−3575. doi: 10.1021/ic010063y
18. [18]
  Chavez D. E.; Hiskey M. A. 1,2,4,5-tetrazine based energetic materials. J. Energetic Mater. 1999, 17, 357−377. doi: 10.1080/07370659908201796
19. [19]
  De Vries L.; Winstein S. Neighboring carbon and hydrogen. XXXIX. 1 Complex rearrangements of bridged ions. Rearrangement leading to the bird-cage hydrocarbon1. J. Am. Chem. Soc. 1960, 82, 5363−5376. doi: 10.1021/ja01505a023
20. [20]
  Liebman J. F.; Greenberg A. A survey of strained organic molecules. Chem. Rev. 1976, 76, 311−365. doi: 10.1021/cr60301a002
21. [21]
  Marchand A. P.; Wu A. Syntheses of new substituted pentacyclo[5.4. 0.02, 6.03, 10.05, 9]undecanes: a novel synthesis of hexacyclo[6.2. 1.13, 6.02, 7.04, 10.05, 9]dodecane (1,3-bishomopentaprismane). J. Org. Chem. 1986, 51, 1897−1900. doi: 10.1021/jo00360a046
22. [22]
  Nielsen A. T.; Nissan R. A.; Vanderah D. J.; Coon C. L.; Gilardi R. D.; George C. F.; Flippen-Anderson J. Polyazapolycyclics by condensation of aldehydes with amines. 2. Formation of 2,4,6,8,10,12-hexabenzyl-2,4,6,8,10,12-hexaazatetracyclo [5.5. 0.05. 9.03, 11] dodecanes from glyoxal and benzylamines. J. Org. Chem. 1990, 55, 1459−1466. doi: 10.1021/jo00292a015
23. [23]
  Schulman J. M.; Disch R. L. Ab initio heats of formation of medium-sized hydrocarbons. The heat of formation of dodecahedrane. J. Am. Chem. Soc. 1984, 106, 1202−1204. doi: 10.1021/ja00317a005
24. [24]
  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. 01.
25. [25]
  Hehre W. J.; Ditchfield R.; Pople J. A. Self−Consistent molecular orbital methods. XII. Further extensions of Gaussian−Type basis sets for use in molecular orbital studies of organic olecules. J. Chem. Phys. 1972, 56, 2257−2261. doi: 10.1063/1.1677527
26. [26]
  Lee C.; Yang W.; Parr R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 1988, 37, 785−789. doi: 10.1103/PhysRevB.37.785
27. [27]
  Schütz M.; Hetzer G.; Werner H.-J. Low-order scaling local electron correlation methods. I. Linear scaling local MP2. J. Chem. Phys. 1999, 111, 5691−5705. doi: 10.1063/1.479957
28. [28]
  Curtiss L. A.; Raghavachari K.; Redfern P. C.; Stefanov B. B. Assessment of complete basis set methods for calculation of enthalpies of formation. J. Chem. Phys. 1998, 108, 692−697. doi: 10.1063/1.475442
29. [29]
  Curtiss L. A.; Raghavachari K.; Redfern P. C.; Pople J. A. Assessment of Gaussian-2 and density functional theories for the computation of enthalpies of formation. J. Chem. Phys. 1997, 106, 1063−1079. doi: 10.1063/1.473182
30. [30]
  Shao J.; Cheng X.; Yang X. Density functional calculations of bond dissociation energies for removal of the nitrogen dioxide moiety in some nitroaromatic molecules. J. Mol. Struct. THEOCHEM 2005, 755, 127−130. doi: 10.1016/j.theochem.2005.08.008
31. [31]
  Politzer P.; Lane P. Comparison of density functional calculations of C–NO₂, N–NO₂ and C–NF₂ dissociation energies. J. Mol. Struct. THEOCHEM 1996, 388, 51−55.
32. [32]
  Harris N. J.; Lammertsma K. Ab initio density functional computations of conformations and bond dissociation energies for hexahydro-1,3,5-trinitro-1,3,5-triazine. J. Am. Chem. Soc. 1997, 119, 6583−6589. doi: 10.1021/ja970392i
33. [33]
  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
34. [34]
  Politzer P.; Ma Y.; Lane P.; Concha M. C. Computational prediction of standard gas, liquid, and solid-phase heats of formation and heats of vaporization and sublimation. Int. J. Quantum Chem. 2005, 105, 341−347. doi: 10.1002/qua.20709
35. [35]
  Owens F. J. Calculation of energy barriers for bond rupture in some energetic molecules. J. Mol. Struct. THEOCHEM 1996, 370, 11−16. doi: 10.1016/S0166-1280(96)04673-8
36. [36]
  Guo L. Density functional study of structural and electronic properties of GaP_n (2 ≤ n ≤ 12) clusters. J. Mater. Sci. 2010, 45, 3381−3387. doi: 10.1007/s10853-010-4361-3
37. [37]
  Fan X.-W.; Ju X.-H. Theoretical studies on four-membered ring compounds with NF₂, ONO₂, N₃, and NO₂ groups. J. Comput. Chem. 2008, 29, 505−513. doi: 10.1002/jcc.20809
38. [38]
  Rice B. M.; Sahu S.; Owens F. J. Density functional calculations of bond dissociation energies for NO₂ scission in some nitroaromatic molecules. J. Mol. Struct. THEOCHEM 2002, 583, 69−72. doi: 10.1016/S0166-1280(01)00782-5
39. [39]
  Zhang J.; Xiao H. Computational studies on the infrared vibrational spectra, thermodynamic properties, detonation properties, and pyrolysis mechanism of octanitrocubane. J. Chem. Phys. 2002, 116, 10674−10683. doi: 10.1063/1.1479136
40. [40]
  Mulliken R. S. Electronic population analysis on LCAO–MO molecular wave functions. I. J. Chem. Phys. 1955, 23, 1833−1840. doi: 10.1063/1.1740588
41. [41]
  Keshavarz M. H.; Pouretedal H. R. Simple empirical method for prediction of impact sensitivity of selected class of explosives. J. Hazard. Mater. 2005, 124, 27−33. doi: 10.1016/j.jhazmat.2005.05.009
42. [42]
  Bulat F.; Toro-Labbé A.; Brinck T.; Murray J.; Politzer P. Quantitative analysis of molecular surfaces: areas, volumes, electrostatic potentials and average local ionization energies. J. Mol. Model. 2010, 16, 1679−1691. doi: 10.1007/s00894-010-0692-x
43. [43]
  Gálvez-Ruiz J. C.; Holl G.; Karaghiosoff K.; Klapötke T. M.; Löhnwitz K.; Mayer P.; Nöth H.; Polborn K.; Rohbogner C. J.; Suter M.; Weigand J. J. Derivatives of 1,5-Diamino-1H-tetrazole: A new family of energetic heterocyclic-based salts. Inorg. Chem. 2005, 44, 4237−4253. doi: 10.1021/ic050104g
44. [44]
  Axenrod T.; Watnick C.; Yazdekhasti H.; Dave P. R. Synthesis of 1,3,3-trinitroazetidine. Tetrahedron Lett. 1993, 34, 677−6680. doi: 10.1016/S0040-4039(00)61650-7
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]
  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]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  Xindi Yang , Cunli Wang , Dongdong Wang , Haijuan Qin , Kuoxi Xu , Guangyan Qing . High efficiency detection of Zn²⁺ through the improved electron density of aromatic π-conjugated bridges. Chinese Chemical Letters, 2026, 37(4): 111215-. doi: 10.1016/j.cclet.2025.111215
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  Yuanhua Xiao , Jinhui Shou , Shiwei Zhang , Ya Shen , Junwei Liu , Dangcheng Su , Yang Kong , Xiaodong Jia , Qingxiang Yang , Shaoming Fang , Xuezhao Wang . Synergistic interlayer confinement and built-in electric field construct reconstruction-inhibited cobalt selenide for robust oxygen evolution at high current density. Chinese Chemical Letters, 2025, 36(11): 111441-. doi: 10.1016/j.cclet.2025.111441
13. [13]
  Xiaoling Qiu , Ruijie Chen , Keren Luo , Xiaoran Wang , Tuan Wang , Pengcheng Shi , Wenlong Cai , Hao Wu . A high-tap-density, particle-nested-bulk bismuth anode for fast-charging sodium-ion batteries. Chinese Chemical Letters, 2026, 37(4): 110792-. doi: 10.1016/j.cclet.2024.110792
14. [14]
  Run Chai , Qiujie Wu , Yongchao Liu , Xiaohui Song , Xuyong Feng , Yi Sun , Hongfa Xiang . A 3D dual layer host with enhanced sodiophilicity as stable anode for high-energy sodium metal batteries. Chinese Chemical Letters, 2025, 36(6): 110007-. doi: 10.1016/j.cclet.2024.110007
15. [15]
  Mingxing Chen , Xue Li , Nian Liu , Zihe Du , Zhitao Wang , Jing Qi . A zinc-nitrate battery for efficient ammonia electrosynthesis and energy output by a high entropy hydroxide catalyst. Chinese Chemical Letters, 2025, 36(10): 111294-. doi: 10.1016/j.cclet.2025.111294
16. [16]
  Fangwen Peng , Zhen Luo , Yingjin Ma , Haibo Ma . Theoretical study of aromaticity reversal in dimethyldihydropyrene derivatives. Chinese Journal of Structural Chemistry, 2024, 43(5): 100273-100273. doi: 10.1016/j.cjsc.2024.100273
17. [17]
  Tingting Du , Siyu Lu , Zongnan Zhu , Mei Zhu , Yan Zhang , Jian Zhang , Jixiang Chen . Pyrazole derivatives: Recent advances in discovery and development of pesticides. Chinese Chemical Letters, 2025, 36(9): 110912-. doi: 10.1016/j.cclet.2025.110912
18. [18]
  Haitao Liu , Youlin Deng , Dan Ling , Lingzhu Chen , Zhichao Jin . Asymmetric catalysis for the synthesis of planar chiral ferrocene derivatives. Chinese Chemical Letters, 2026, 37(3): 111793-. doi: 10.1016/j.cclet.2025.111793
19. [19]
  Xinghong Cai , Qiang Yang , Yao Tong , Lanyin Liu , Wutang Zhang , Sam Zhang , Min Wang . AlO₂: A novel two-dimensional material with a high negative Poisson's ratio for the adsorption of volatile organic compounds. Chinese Chemical Letters, 2025, 36(2): 109586-. doi: 10.1016/j.cclet.2024.109586
20. [20]
  Huyi Yu , Renshu Huang , Qian Liu , Xingfa Chen , Tianqi Yu , Haiquan Wang , Xincheng Liang , Shibin Yin . Te-doped Fe3O4 flower enabling low overpotential cycling of Li-CO2 batteries at high current density. Chinese Journal of Structural Chemistry, 2024, 43(3): 100253-100253. doi: 10.1016/j.cjsc.2024.100253

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1555)
HTML views(57)

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