Unexpected formation of (trinitromethyl)pyrazines

Yudin, Igor L.; Палысаева, Надежда В.; Аверкиев, Борис Б.; Sheremetev, Aleksei B.

doi:10.1016/j.mencom.2015.05.011

Cited by 5 publications

(2 citation statements)

References 26 publications

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“…Compared with trinitromethyl, the energetic group dinitromethyl is more stable in terms of its molecular structure. 5 Based on the advantages of pyrazole and the dinitromethyl group, combining them to construct new energetic materials with high detonation properties is an ideal strategy. In general, the anion of dinitromethyl can be obtained by reacting trinitromethyl or dinitromethyl ester groups with an alkaline solution.…”

Section: Introductionmentioning

confidence: 99%

Simple methods for the introduction of nitrate ester, amino and diazo-oxide substituents into dinitromethylpyrazole

Zhang

Lin

2022

New J. Chem.

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Section: Introductionmentioning

confidence: 99%

Simple methods for the introduction of nitrate ester, amino and diazo-oxide substituents into dinitromethylpyrazole

Zhang

Lin

2022

New J. Chem.

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“…This compound is an oxidant and has a high density (2.00 g/cm 3 ), but it is unstable in the air and very easy to hydrolyze. Trinitromethyl-substituted pyrazine was also obtained as an unexpected product by the treatment of 2-alkoxy-3-methylpyrazine with an HNO 3 /H 2 SO 4 mixture [ 19 ]. The attachment of trinitromethyl groups with a pyridine ring has also been attempted by different techniques.…”

Section: Introductionmentioning

confidence: 99%

Energetic Di- and Trinitromethylpyridines: Synthesis and Characterization

Zhang

Sun

et al. 2017

Molecules

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Pyridine derivatives based on the addition of trinitromethyl functional groups were synthesized by the reaction of N2O4 with the corresponding pyridinecarboxaldoximes, then they were converted into dinitromethylide hydrazinium salts. These energetic compounds were fully characterized by IR and NMR spectroscopy, elemental analysis, differential scanning calorimetry (DSC), and X-ray crystallography. These pyridine derivatives have good densities, positive enthalpies of formation, and acceptable sensitivity values. Theoretical calculations carried out using Gaussian 03 and EXPLO5 programs demonstrated good to excellent detonation velocities and pressures. Each of these compounds is superior in performance to TNT, while 2,6-bis(trinitromethyl)pyridine (D = 8700 m·s−1, P = 33.2 GPa) shows comparable detonation performance to that of RDX, but its thermal stability is too low, making it inferior to RDX.

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Novel Highly Energetic Pyrazoles: N‐Trinitromethyl‐Substituted Nitropyrazoles

Далингер

Вацадзе

Шкинева

et al. 2015

Chemistry An Asian Journal

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A new family of energetic compounds, nitropyrazoles bearing a trinitromethyl moiety at the nitrogen atom of the heterocycle, was designed. The desirable high-energy dense oxidizers 3,4-dinitro- and 3,5-dinitro-1-(trinitromethyl)pyrazoles were synthesized in good yields by destructive nitration of the corresponding 1-acetonylpyrazoles. All of the prepared compounds were fully characterized by multinuclear NMR and IR spectroscopy, as well as by elemental analysis. Single-crystal X-ray diffraction studies show remarkably high density. Impact sensitivity tests and thermal stability measurements were also performed. All of the pyrazoles possess positive calculated heats of formation and exhibit promising energetic performance that is the range of 1,3,5-trinitroperhydro-1,3,5-triazine and pentaerythritol tetranitrate. The new pyrazoles exhibit positive oxygen balance and are promising candidates for new environmentally benign energetic materials.

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Unexpected formation of (trinitromethyl)pyrazines

Cited by 5 publications

References 26 publications

Simple methods for the introduction of nitrate ester, amino and diazo-oxide substituents into dinitromethylpyrazole

Simple methods for the introduction of nitrate ester, amino and diazo-oxide substituents into dinitromethylpyrazole

Energetic Di- and Trinitromethylpyridines: Synthesis and Characterization

Novel Highly Energetic Pyrazoles: N‐Trinitromethyl‐Substituted Nitropyrazoles

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