Citation: Jing YANG, Yu PANG, Min-Xian LI, Ge-Fei YANG, Jing-Xian JIA, Xiang-Jun MENG, Li-Hua LIU, Xiao-Chun YANG, Xiao-Zhen GAO. Molecular Design and Property Prediction of High Density 4-Nitro-5-(5-nitro-1, 2, 4-triazol-3-yl)-2H-1, 2, 3-triazolate Derivatives as the Potential High Energy Explosives[J]. Chinese Journal of Structural Chemistry, ;2022, 41(2): 220212. doi: 10.14102/j.cnki.0254-5861.2011-3256 shu

Molecular Design and Property Prediction of High Density 4-Nitro-5-(5-nitro-1, 2, 4-triazol-3-yl)-2H-1, 2, 3-triazolate Derivatives as the Potential High Energy Explosives

a.
Department of Chemistry, Tangshan Normal College, Tangshan 063000, China
b.
School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China
c.
Yangquan Municipal Key Laboratory of Quantum Manipulation, Shanxi Institute of Technology, Yangquan 045000, China

Corresponding author: Jing YANG, yjlzddove@gmail.com
Received Date: 10 June 2021
Accepted Date: 14 August 2021

Fund Project: the Foundation Project of Tangshan Normal University 2021B37the Foundation Project of Tangshan Normal University 2021B32the School Fund of Shanxi Institute of Technology 2019004the Fund of Shanxi Provincial Education Department 2019L0986

Figures(1)

To search for potential energetic materials with large energy density and acceptable thermodynamics and kinetics stability, twelve derivatives of 4-nitro-5-(5-nitro-1, 2, 4-triazol-3-yl)-2H-1, 2, 3-triazolate (named A~L) are designed and analyzed by using density functional theory (DFT) calculations at the B3LYP/6-311G** level of theory. The molecular heats of formation (HOF), electronic structures, impact sensitivity (H₅₀), oxygen balance (OB) and density (ρ) are investigated by isodesmic reaction method and physicochemical formulas. Furthermore, the detonation velocity (D) and detonation pressure (P) are calculated to study the detonation performance by Kamlet-Jacobs (K-J) equation. These results show that new molecule J (H₅₀ = 36.9 cm, ρ = 1.90 g/cm³, Q = 1912.46 cal/g, P = 37.82 GPa, D = 9.22 km/s, OB = 0.00), compound A (H₅₀ = 27.9 cm, ρ = 1.93 g/cm³, Q = 1612.93 cal/g, P = 38.90 GPa, D = 9.19 km/s) and compound H (H₅₀ = 37.3 cm, ρ = 1.97 g/cm³, Q = 1505.06 cal/g, P = 37.20 GPa, D = 9.01 km/s) present promising effects that are far better RDX and HMX as the high energy density materials. Our calculations can provide useful information for the molecular synthesis of novel high energy density materials.
- 4-nitro-5-(5-nitro-1, 2, 4-triazol-3-yl)-2H-1, 2, 3-triazolate,
- energetic materials,
- density functional theory,
- explosive
1. [1]
  Tang, Y. X.; Huang, W.; Chinnam, A. K.; Singh, J. S.; Staples, R. J.; Shreeve, J. M. Energetic tricyclic polynitropyrazole and its salts: proton-locking effect of guanidium cations. Inorg. Chem. 2021, 60, 8339−8345. doi: 10.1021/acs.inorgchem.1c01202
2. [2]
  Zhang, W. Q.; Zhang, J. H.; Deng, M. C.; Qi, X. J.; Nie, F. D.; Zhang, Q. H. A promising high-energy-density material. Nat. Commun. 2017, 8, 181−187. doi: 10.1038/s41467-017-00286-0
3. [3]
  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.
4. [4]
  He, P.; Zhang, J. G.; Wang, K.; Yin, X.; Jin, X.; Zhang, J. G. Extensive theoretical studies on two new members of the FOX-7 family: 5-(dinitromethylene)-1, 4-dinitramino-tetrazole and 1, 1΄-dinitro-4, 4΄-diamino-5, 5′-bitetrazole as energetic compounds. Phys. Chem. Chem. Phys. 2015, 17, 5840−5848. doi: 10.1039/C4CP04883K
5. [5]
  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
6. [6]
  Tang, Y. X.; He, C. L.; Imler, G. H.; Parrish, D. A.; Shreeve, J. M. Aminonitro groups surrounding a fused pyrazolotriazine ring: a superior thermally stable and insensitive energetic material. ACS Appl. Energy Mater. 2019, 2, 2263−2267. doi: 10.1021/acsaem.9b00049
7. [7]
  Xu, Z.; Cheng, G. B.; Zhu, S. G.; Lin, Q. H.; Yang, H. W. Nitrogen-rich salts based on the combination of 1, 2, 4-triazole and 1, 2, 3-triazole rings: a facile strategy for fine tuning energetic properties. J. Mater. Chem. A 2018, 6, 2239–2248. doi: 10.1039/C7TA08941D
8. [8]
  Hehre, W. J.; Ditchfield, D.; Radom, L.; Pople, J. A. Molecular orbital theory of the electronic structure of organic compounds. V. Molecular theory of bond separation. J. Am. Chem. Soc. 1970, 92, 4796–4801. doi: 10.1021/ja00719a006
9. [9]
  Zhang, J. C.; Zhang, J. H.; Imler, G. H.; Parrish, D. A.; Shreeve, J. M. Sodium and potassium 3, 5-dinitro-4-hydropyrazolate: three dimensional metal-organic frameworks as promising super-heatresistant explosives. ACS Appl. Energy Mater. 2019, 2, 7628–7634. doi: 10.1021/acsaem.9b01608
10. [10]
  Wang, Q.; Shao, Y. L.; Lu, M. C₈N₁₂O₈: a promising insensitive high-energy-density material. Cryst. Growth Des. 2018, 18, 6150–6154. doi: 10.1021/acs.cgd.8b01016
11. [11]
  Li, B. T.; Li, L. L.; Peng, J. Theoretical exploration about the detonation performance and thermal stability of the nitro-substituted derivatives of guanine. Chin. J. Struct. Chem. 2021, 40, 409–414.
12. [12]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B. G.; Petersson, A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery Jr. J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D. 01, Gaussian, Inc., Wallingford CT 2009.
13. [13]
  He, P.; Zhang, J. G.; Wang, K.; Yin, X.; Zhang, J. G. Computational studies on two novel energetic nitrogen-rich compounds based on tetrazolone. J. Phys. Org. Chem. 2015, 3484–3489.
14. [14]
  Politzer, P.; Lane, P.; Murray, J. S. Computational characterization of a potential energetic compound: 1, 3, 5, 7-tetranitro-2, 4, 6, 8-tetraazacubane. Cent. Eur. J. Energ. Mater. 2011, 8, 39–52.
15. [15]
  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
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]
  Politzer, P.; Murray, J. S. The fundamental nature and role of the electrostatic potential in atoms and molecules. Theor. Chem. Acc. 2002, 108, 134–142. doi: 10.1007/s00214-002-0363-9
18. [18]
  Pospíšil, M.; Vávra, P.; Concha, M. C.; Murray, J. S.; 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
19. [19]
  Rice, B. M.; Hare, J. J. A quantum mechanical investigation of the relation between impact sensitivity and the charge distribution in energetic molecules. J. Phys. Chem. A 2002, 106, 1770–1783. doi: 10.1021/jp012602q
20. [20]
  Christe, K. O.; Wilson, W. W.; Sheehy, J. A.; Boatz, J. A. N⁵⁺: a novel homoleptic polynitrogen ion as a high energy density material. Angew. Chem. Int. Ed. 1999, 38, 2004–2009. doi: 10.1002/(SICI)1521-3773(19990712)38:13/14<2004::AID-ANIE2004>3.0.CO;2-7
21. [21]
  Song, X. L.; Li, J. C.; Hou, H.; Wang, B. S. Extensive theoretical studies of a new energetic material: tetrazino-tetrazine-tetraoxide (TTTO). J. Comput. Chem. 2009, 30, 1816–1820. doi: 10.1002/jcc.21182
22. [22]
  Guo, C.; Zhang, H.; Wang, X.; Liu, X.; Sun, J. Study on a novel energetic cocrystal of TNT/TNB. J. Mater. Sci. 2013, 48, 1351–135. doi: 10.1007/s10853-012-6881-5
23. [23]
  Li, B. T.; Li, L. L.; He, J. X. Looking for high energy density molecules in the nitro-substituted derivatives of pyridazine. Chin. J. Struct. Chem. 2020, 39, 849–854
24. [24]
  Politzer, P.; Murray, J. S. Some perspectives on estimating detonation properties of C, H, N and O compounds. Cent. Eur. J. Energ. Mater. 2011, 8, 209–220.
25. [25]
  Zhang, C.; Shu, Y.; Huang, Y.; Zhao, X.; Dong, H. Investigation of correlation between impact sensitivities and nitro group charges in nitro compounds. J. Phys. Chem. B 2005, 109, 8978–8982. doi: 10.1021/jp0512309
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