Citation: Lian ZENG, Yu-He JIANG, Jin-Ting WU, Hong-Bo LI, Jian-Guo ZHANG. Molecular Design and Performance Studies of 4-(1, 2, 4-Triazole-5-yl) Furazan Derivatives as Promising Energetic Materials[J]. Chinese Journal of Structural Chemistry, ;2021, 40(7): 942-948. doi: 10.14102/j.cnki.0254–5861.2011–3061 shu

Molecular Design and Performance Studies of 4-(1, 2, 4-Triazole-5-yl) Furazan Derivatives as Promising Energetic Materials

Lian ZENG ^a ,
Yu-He JIANG ^a ,
Jin-Ting WU ^{a, b,,} ,
Hong-Bo LI ^a,, ,
Jian-Guo ZHANG ^b

a.
School of Materials Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, China
b.
State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, China

Corresponding author: Jin-Ting WU, wjt1234@163.com Hong-Bo LI, li-honggg@163.com
Received Date: 10 December 2020
Accepted Date: 25 January 2021

Fund Project: the Opening Project of State Key Laboratory of Explosion Science and Technology (Beijing Institute of Technology) KFJJ20-03MDoctoral Foundation of SWUST 17zx7128Major Special Projects of the Equipment Development Department of the Central Military Commission of China 14021001040305-5

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In this paper, eight 4-(1, 2, 4-triazole-5-yl) furazan (TZFZ) derivatives were designed, and the molecular configurations of TZFZ compounds were optimized by using the B3LYP/6-311+G* level. Meanwhile, the detonation performance, density, impact sensitivity, heat of formation and oxygen balance have been investigated. The results clearly and intuitively illustrate that the introduction of -NO₂ and coordination oxygen plays a pivotal role in increasing the density and heat of formation. In summary, the properties of these compounds are better than the traditional explosives RDX and TNT, especially the density and detonation pressure. Energetic evaluations showed that compounds B1 (P = 36.73 GPa; D = 8.98 km·s^-1, ρ = 1.88 g·cm^-3) and B7 (P = 38.51 GPa; D = 9.17 km·s^-1, ρ = 1.90 g·cm^-3) could be seen as promising candidates of energetic insensitive compounds with remarkable performance.
- density functional theory,
- 4-(1, 2, 4-triazole-5-yl)furazan derivatives,
- performance prediction,
- molecular design
1. [1]
  Yu, Q.; Yang, H. W.; Imler, G. H.; Parrish, D. A.; Cheng, G. B.; Shreeve, J. M. Derivatives of 3, 6-bis(3-aminofurazan-4-ylamino)-1, 2, 4, 5-tetrazine: excellent energetic properties with lower sensitivities. Acs. Appl. Mater. Inter. 2020, 12, 31522−31531. doi: 10.1021/acsami.0c08526
2. [2]
  Malow, M.; Wehrstedt, K. D.; Neuenfeld, S. On the explosive properties of 1H-benzotriazole and 1H-1, 2, 3-triazole. Tetrahedron Lett. 2007, 48, 1233−1235. doi: 10.1016/j.tetlet.2006.12.046
3. [3]
  Li, X. H.; Zhang, R. Z.; Zhang, X. Z. Theoretical studies on a series of 1, 2, 3-triazoles derivatives as potential high energy density compounds. Struct. Chem. 2011, 22, 577−587. doi: 10.1007/s11224-011-9734-y
4. [4]
  Jin, R. Y.; Zeng, C. Y.; Liang, X. H.; Sun, X. H.; Liu, Y. F.; Wang, Y. Y.; Zhou, S. Design, synthesis, biological activities and DFT calculation of novel 1, 2, 4-triazole Schiff base derivatives. Bioorg. Chem. 2018, 80, 253−260. doi: 10.1016/j.bioorg.2018.06.030
5. [5]
  Du, L. X. S.; Liu, Y. C.; Cheng, G. M.; Luo, J. Molecular design and property study of xifurza type fused cast explosive. Acta Armamentarii 2018, 39, 46−56. doi: 10.3969/j.issn.1000-1093.2018.01.005
6. [6]
  Jin, X. H.; Zhou, J. H.; Hu, B. C. Exploration of high-energy-density materials: computational insight into energetic derivatives based on 1, 2, 4, 5-tetrahydro-1, 2, 4, 5-tetrazine. Chemistryopen 2018, 7, 780−788. doi: 10.1002/open.201800161
7. [7]
  Sun, S. Y.; Lu, M. Conjugation in multi-tetrazole derivatives: a new design direction for energetic materials. J. Mol. Model. 2018, 24, 173−182. doi: 10.1007/s00894-018-3710-z
8. [8]
  Dalinger, I. L.; Kormanov, A. V.; Suponitsky, K. Y.; Muravyev, N. V.; Sheremetev, A. B. Pyrazole-tetrazole hybrid with trinitromethyl, fluorodinitromethyl, or (difluoroamino) dinitromethyl groups: high-performance energetic materials. Chem. Asian J. 2018, 13, 1165−1172. doi: 10.1002/asia.201800214
9. [9]
  Xu, Z.; Cheng, G.; Yang, H.; Zhang, J.; Shreeve, J. N. M. Synthesis and characterization of 4-(1, 2, 4-triazole-5-yl)furazan derivatives as high-performance insensitive energetic materials. Chem. Eur. J. 2018, 24, 10488−10497. doi: 10.1002/chem.201801597
10. [10]
  Zhai, L. J.; Wang, B. Z.; Fan, X. Z. Synthesis and property estimation of 3, 3΄-bis (tetrazole-5-yl)-4, 4΄-azotaxime. Chin. J. Explos. Propellants 2016, 41, 21−25.
11. [11]
  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.
12. [12]
  Politzer, P.; Martinez, J.; Murray, J. S.; Concha, M. C.; Toro-Labbe, A. An electrostatic interaction correction for improved crystal density prediction. Mol. Phys. 2009, 107, 2095−2101. doi: 10.1080/00268970903156306
13. [13]
  Politzer, P.; Murray, J. S. Some perspectives on estimating detonation properties of C, H, N, O compounds. Cent. Eur. J. Energ. Mater. 2011, 8, 209−220.
14. [14]
  Kamlet, M. J.; Ablard, J. E. Chemistry of detonations. II. Buffered equilibria. J. Chem. Phys. 1968, 48, 36−42. doi: 10.1063/1.1667930
15. [15]
  Kamlet, M. J.; Dickinson, C. Chemistry of detonations. III. Evaluation of the simplified calculational method for Chapman-Jouguet detonation pressures on the basis of available experimental information. J. Chem. Phys. 1968, 48, 43−50. doi: 10.1063/1.1667939
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]
  He, P.; Zhang, J. G.; Wu, L.; Wu, J. T.; Zhang, T. L. Computational design and screening of promising energetic materials: novel azobis(tetrazoles) with ten catenated nitrogen atoms chain. J. Phys. Org. Chem. 2016, 30, 36−74.
18. [18]
  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. 2002, 106, 1770−1783. doi: 10.1021/jp012602q
19. [19]
  Lu, T.; Chen, F. Multiwfn: a multifunctional wavefunction analyzer. J. Comput. Chem. 2012, 33, 580−592. doi: 10.1002/jcc.22885
20. [20]
  Byrd, E. F. C.; Rice, B. M. Improved prediction of heats of formation of energetic materials using quantum mechanical calculations. J. Phys. Chem. 2006, 110, 1005−1013. doi: 10.1021/jp0536192
21. [21]
  Joo, Y. H.; Shreeve, J. M. High-density energetic mono-or bis(oxy)-5-nitroiminotetrazoles. Angew. Chem. Int. Ed. 2010, 49, 7320−7323. doi: 10.1002/anie.201003866
22. [22]
  Lewczuk, R.; Ksiazek, M.; Katarzyna, G. S.; Katarzyna, C. Azo-linked high-nitrogen energetic materials. J. Mater. Chem. A 2018, 6, 1915−1940. doi: 10.1039/C7TA09593G
23. [23]
  Wu, Q.; Zhu, W.; Xiao, H. Molecular design of trinitromethyl-substituted nitrogen-rich heterocycle derivatives with good oxygen balance as high-energy density compounds. Struct. Chem. 2013, 24, 1725−1736. doi: 10.1007/s11224-013-0217-1
24. [24]
  Wei, T.; Wu, J.; Zhu, W.; Zhang, C.; Xiao, H. Characterization of nitrogen-bridged 1, 2, 4, 5-tetrazine-furazan-and 1H-tetrazole-based polyheterocyclic compounds: heats of formation, thermal stability, and detonation properties. J. Mol. Model. 2012, 18, 3467−3479. doi: 10.1007/s00894-012-1357-8
25. [25]
  Lian, P.; Lai, W. P.; Lu, J.; Liu, Y. Z.; Wei, T.; Wang, B. Z. Study on density functional theory of trifurozan oxyheterocyclic hepttriene. Comput. Appl. Chem. 2016, 33, 910−914.
26. [26]
  Ghule, V. D. Computational studies on the triazole-based high energy materials. Comput. Theor. Chem. 2012, 992, 92−96. doi: 10.1016/j.comptc.2012.05.007
27. [27]
  Li, J. A multivariate relationship for the impact sensitivities of energetic N-nitrocompounds based on bond dissociation energy. J. Hazard. Mater. 2010, 174, 728−733. doi: 10.1016/j.jhazmat.2009.09.111
28. [28]
  Zhang, C. Y. Review of the establishment of nitro group charge method and its applications. J. Hazard. Mater. 2009, 161, 21−28. doi: 10.1016/j.jhazmat.2008.04.001
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