Combining 5,6-fused triazolo-triazine with pyrazole: A novel energetic framework for heat-resistant explosive

Zhang, Guojie; Hu, Wei; Ma, Jinchao; Yang, Hongwei

doi:10.1016/j.cej.2021.131297

Cited by 28 publications

(29 citation statements)

References 46 publications

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“…As shown in Figure , compared with 8 , compound 9 exhibits a lower maximum ESP value. In general, the higher the positive charge, the lower the thermal stability of the compound, which indicates that compound 9 is more stable than 8 .…”

Section: Resultsmentioning

confidence: 99%

“…22 As shown in Figure 6, compared with 8, compound 9 exhibits a lower maximum ESP value. In general, the higher the positive charge, the lower the thermal stability of the compound, 23 which indicates that compound 9 is more stable than 8. As inter-and intramolecular interactions are closely related to thermal stability and sensitivities, the noncovalent interactions (NCI) 24 of 8 and 9 were chosen, calculated, and visualized by Multiwfn and VMD software.…”

Section: T H Imentioning

confidence: 99%

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Silver-Catalyzed Synthesis of 2-Cyano-5-pyrazolyl-2H-tetrazole: A Promising Precursor to Insensitive Energetic Compounds

Dong

Liu

Lyu

et al. 2022

Crystal Growth & Design

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Exploring new synthetic strategies for designing energetic molecules is one of the key factors in promoting the development of energetic materials. In this study, we report a simple and efficient method for constructing a novel energetic skeleton (2) via silver catalysis. A series of pyrazole-tetrazole energetic derivatives were successfully synthesized using 2-cyano-5-pyrazolyl-2H-tetrazole (2) as a base skeleton. These energetic compounds were fully characterized by nuclear magnetic resonance (NMR) spectroscopy, IR spectroscopy, and elemental analysis. The structures of compounds 5, 6, 8, and 9 were determined by single-crystal X-ray diffraction. The physicochemical properties and detonation performances of all newly synthesized energetic compounds were studied. All new compounds show better detonation performances and lower sensitivities compared with TNT. The detonation performances of compound 10 are close to those of RDX.

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Section: Resultsmentioning

confidence: 99%

Section: T H Imentioning

confidence: 99%

Silver-Catalyzed Synthesis of 2-Cyano-5-pyrazolyl-2H-tetrazole: A Promising Precursor to Insensitive Energetic Compounds

Dong

Liu

Lyu

et al. 2022

Crystal Growth & Design

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“…By plotting the distribution of localized orbital locator-π (LOL-π) electrons, 19 delocalized electron clouds are found in all atoms in 2 and 5 (Figure 5). As shown in Figure 5a, the whole molecular skeleton, bonded nitro group, amino group, and azido group are distributed π-electrons.…”

Section: Physicochemical and Energeticmentioning

confidence: 99%

Series of Azido and Fused-Tetrazole Explosives: Combining Good Thermal Stability and Low Sensitivity

Lei

Yang

Zhang

2022

ACS Appl. Mater. Interfaces

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The introduction of azido groups into the energetic skeleton has the advantages of increasing the energy level. In this work, a series of azido compounds with good stability and low sensitivity as well as tetrazole-fused compounds based on energetic salts are synthesized. The detonation pressures and velocities of these new compounds fall in the ranges of 18.9–27.3 GPa and 7153–8450 m s–1, respectively. The detonation velocity of the tetrazole-fused compounds based on the potassium salts 3, 6, and 7 are 7810, 7153, and 7989 m s–1, respectively. Also, their decomposition temperatures (244, 237, and 240 °C, respectively) are higher than that of traditional explosive RDX (204 °C). Notably, two representative compounds 2 and 5 possess higher decomposition temperature (2: 196 °C and 5: 178 °C) and overall detonation properties (2: D = 8129 m s–1 and P = 26.6 GPa and 5: D = 8336 m s–1 and P = 27.3 GPa) as well as relativity lower sensitivities (2: IS = 12 J and FS = 240 N and 5: IS = 10 J and FS = 144 N) than that of primary explosive 2-diazo-4,6-dinitrophenol (T d = 157 °C, D = 6900 m s–1, P = 24.7 GPa, IS = 1 J, and FS = 24.7 N). Moreover, the initiation capacity of compounds 2 and 5 was also assessed through the initiation tests. The results indicate that the two compounds could be a promising environmentally friendly primary explosive.

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“…From TNBP (C–C bonded pyrazole) to TNAP (C–NN–C bridged pyrazole), the mechanical sensitivities have a remarkable decrease. In order to understand the inherent factors of mechanical sensitivity, based on the optimized structure of TNAP and TNBP, multicenter bond orders and LOL-π (localized orbital locator-π) were calculated to evaluate their aromaticity. − As shown in Figure a,b, the calculated multicenter bond orders of the pyrazole ring in TNAP (0.5773) are higher than that in TNBP (0.5458), which indicates that the newly synthesized azopyrazole energetic compound (TNAP) shows better aromaticity than TNBP. The LOL-π isosurface graphs are given in Figure b,e.…”

Section: Crystal Structure Analysismentioning

confidence: 99%

Polynitro-Functionalized Azopyrazole with High Performance and Low Sensitivity as Novel Energetic Materials

Cheng

Yang

2022

ACS Appl. Mater. Interfaces

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The development of energetic materials is still facing a huge challenge because the relationship between energy and sensitivity is usually contradictory: high energy is always accompanied with low sensitivity. Here, a high-energy, low-sensitivity energetic polynitro-functionalized azopyrazole (TNAP) and its energetic salts have been synthesized. The structural characterization of these compounds was analyzed by elemental analysis, 1H and 13C NMR spectroscopies, and infrared spectroscopy. The single-crystal structure of compounds K2TNAP, TNAP, 5, and 6 was obtained by X-ray diffraction, and K2TNAP is a novel energetic metal–organic framework. The calculated detonation properties of TNAP (9040 m s–1 and 36.0 GPa) are superior to that of RDX (8796 m s–1 and 33.6 GPa). In addition, TNAP also has lower mechanical sensitivity (IS > 40 J, FS = 244 N) and higher decomposition temperature (Td = 221 °C) than RDX (IS = 7.4 J, FS = 120 N, and Td = 204 °C). These experimental results suggest that TNAP may become a new candidate for secondary explosives.

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Combining 5,6-fused triazolo-triazine with pyrazole: A novel energetic framework for heat-resistant explosive

Cited by 28 publications

References 46 publications

Silver-Catalyzed Synthesis of 2-Cyano-5-pyrazolyl-2H-tetrazole: A Promising Precursor to Insensitive Energetic Compounds

Silver-Catalyzed Synthesis of 2-Cyano-5-pyrazolyl-2H-tetrazole: A Promising Precursor to Insensitive Energetic Compounds

Series of Azido and Fused-Tetrazole Explosives: Combining Good Thermal Stability and Low Sensitivity

Polynitro-Functionalized Azopyrazole with High Performance and Low Sensitivity as Novel Energetic Materials

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