Polynitro-<i>N</i>-aryl-C-nitro-pyrazole/imidazole Derivatives: Thermally Stable-Insensitive Energetic Materials

Vangara, Srinivas; Kommu, Nagarjuna; Thaltiri, Vikranth; Balaraju, M; Sahoo, Akhila K.

doi:10.1021/acs.joc.2c00410

Cited by 19 publications

(17 citation statements)

References 55 publications

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“…Therefore, new energetic compounds with both higher energy and better stability might be achieved by constructing a conjugation system based on polynitrobenzene and azole ring. 23 good energetic properties by constructing a conjugated system. 24 Some other energetic compounds based on polynitrobenzene and azole rings have also been reported such as 5-picrylamino-tetrazole(I) and 3-amino-5-picrylamino-1,2,4-triazole (APATO), and all these compounds exhibit good thermal stability (Figure 1).…”

Section: ■ Introductionmentioning

confidence: 99%

“…On the contrary, azole rings usually exhibit excellent energetic properties, but they show poor thermal stability and high sensitivities. Therefore, new energetic compounds with both higher energy and better stability might be achieved by constructing a conjugation system based on polynitrobenzene and azole ring . For instance, PATO has achieved good stability while maintaining good energetic properties by constructing a conjugated system .…”

Section: Introductionmentioning

confidence: 99%

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Bicyclic High-Energy and Low-Sensitivity Regioisomeric Energetic Compounds Based on Polynitrobenzene and Pyrazoles

Zhang

et al. 2023

Crystal Growth & Design

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With the development of synthetic methodology and crystallography of energetic materials, regiochemistry is becoming popular and vital in the design of versatile energetic compounds as well as in the thorough research on the relationship between structure and property. In this study, two regioisomeric bicyclic energetic compounds based on pyrazole and polynitrobenzene were synthesized simultaneously by a simple synthetic route, and the regioisomers could be purified by a facile approach. It is interesting to note that the ratio of the two compounds changed with temperature. From 80 to 110 °C, the proportion of compound 2 gradually enhanced with the increase in temperature. In addition, the nitramine product of compound 1 was also synthesized. The structural data of compounds 1, 2, and 3 were confirmed by X-ray single-crystal diffraction. The detonation velocities of the new compounds are in the range of 8436–8788 m s–1 and impact sensitivities are between 15 and 27.5 J, of which compounds 2 and 3 not only present superior sensitivities to those of the classical high-energy explosive RDX (7.5 J) but also exhibit comparable detonation velocities to the measured RDX powder (V D = 8796 m s–1), calculated by EXPLO5 as 8788 and 8526 m s–1, respectively. Moreover, compounds 1 and 2 show good thermal stability with decomposition temperatures up to 263 and 287 °C, which is higher than that of RDX (T dec: 204 °C). All of the above information indicates that these compounds are high-energy, low-sensitivity energetic materials featuring prospective applications.

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Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Bicyclic High-Energy and Low-Sensitivity Regioisomeric Energetic Compounds Based on Polynitrobenzene and Pyrazoles

Zhang

et al. 2023

Crystal Growth & Design

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“…In addition, a benzene ring can improve the thermal stability of the whole molecule due to its stabilizing and conjugating effect, , such as 2,4,6-trinitrotoluene (TNT, T d = 295 °C, Figure a). In recent years, focuses have been concentrated on exploring the reaction between polynitrobenzene rings and nitrogen-rich heterocyclic rings. − The results show that the introduction of polynitrobenzene rings is beneficial to improving the overall thermal stability of the compound, and the combination of nitrogen-rich heterocyclic rings yields heat-resistant explosives with good detonation performances (Figure b). However, the introduction of a benzene ring reduces the nitrogen content and produces certain pollution, which limits its further application.…”

Section: Introductionmentioning

confidence: 99%

Highly Thermally Stable Energetic Compounds Based on 6-Amino-5-nitropyrimidine

Wang

Zhao

Huang

et al. 2023

Crystal Growth & Design

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Two energetic materials (2 and 4) were designed and synthesized from 3,5-diamino-1,2,4-triazole (DAT) and 3,5-diamino-4-nitropyrazole (DANP) as starting materials. Both of them were fully characterized by NMR spectroscopy, IR spectroscopy, and single-crystal X-ray diffraction analysis. Compounds 2 (T d = 295 °C) and 4 (T d = 300 °C) exhibit good thermal stabilities by differential scanning calorimetry. The detonation performances (2: D = 7281 m s–1, P = 18.6 GPa; 4: D = 7436 m s–1, P = 20.5 GPa) were calculated by EXPLO5 software. Their mechanical sensitivities (2: IS > 20 J, FS = 360 N; 4: IS > 20 J, FS = 360 N) were measured by BAM standard tests. Both 2 and 4 exhibited high thermal stabilities, insensitive characteristics, and fair detonation performances, which give them good potential as heat-resistant explosives.

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“…TNT (2,4,6‐trinitrotoluene) and TATB (2,4,6‐triamino‐1,3,5‐trinitrobenzene) are examples based on polynitroarene utilized as conventional explosives in the military and civilian sectors [10] . Various energetic compounds with polynitroarene and energetic heterocycles (azoles and oxadiazoles) connected with C−N bonds have been reported in recent years [31,32] . The synthetic procedure of these C−N connected polynitroarene‐nitroazole systems includes direct nucleophilic substitution at the chloropolynitroarene with azole moieties.…”

Section: Introductionmentioning

confidence: 99%

“…Figure 2. Energetic amino(dinitro)benzene and dinitropyrazole moieties connected with C-N[32] and CÀ C bonds.…”

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confidence: 99%

Connecting Energetic Nitropyrazole and Nitrobenzene Moieties with C−C Bonds using Suzuki Cross‐Coupling Reaction: A Novel Route to Thermally Stable Energetic Materials

et al. 2022

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This work describes a new route to thermally stable energetic materials by connecting different types of energetic moieties (nitropyrazole and polynitrobenzene) with C−C bonds, where the first step involves a Suzuki cross‐coupling reaction between 4‐bromo‐3,5‐dinitro‐1H‐pyrazole and 4‐chlorophenylboronic acid. Further nitration, amination, oxidation, and salt formation reactions on the resulting C−C coupled framework resulted in various thermally stable energetic materials. All the compounds were fully characterized using IR, NMR [1H, 13C{1H}], differential scanning calorimetry (DSC), elemental analysis, and HRMS studies. Compounds 7 and 9 were further characterized by 15N NMR, and compounds 3 and 6 were characterized by single‐crystal X‐ray diffraction studies. Theoretical heats of formation and energetic performance for all the energetic compounds were calculated using Gaussian 09 and EXPLO5 v6.06 programs, respectively. This research introduces a novel method for synthesizing C−C coupled energetic materials that are not accessible by any other routes.

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Polynitro-N-aryl-C-nitro-pyrazole/imidazole Derivatives: Thermally Stable-Insensitive Energetic Materials

Cited by 19 publications

References 55 publications

Bicyclic High-Energy and Low-Sensitivity Regioisomeric Energetic Compounds Based on Polynitrobenzene and Pyrazoles

Bicyclic High-Energy and Low-Sensitivity Regioisomeric Energetic Compounds Based on Polynitrobenzene and Pyrazoles

Highly Thermally Stable Energetic Compounds Based on 6-Amino-5-nitropyrimidine

Connecting Energetic Nitropyrazole and Nitrobenzene Moieties with C−C Bonds using Suzuki Cross‐Coupling Reaction: A Novel Route to Thermally Stable Energetic Materials

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