Dalinger Igor L, Vatsadze Irina A, Shkineva Tatyana K, Kormanov Alexandr V, Struchkova Marina I, Suponitsky Kyrill Yu, Bragin Anatoly A, Monogarov Konstantin A, Sinditskii Valery P, Sheremetev Aleksei B
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky pr., Moscow, 119991, Russian Federation.
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Science, 28 Vavilov str., Moscow, 119991, Russian Federation.
Chem Asian J. 2015 Sep;10(9):1987-96. doi: 10.1002/asia.201500533. Epub 2015 Jul 14.
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.
设计了一类新型含能化合物，即杂环氮原子上带有三硝基甲基部分的硝基吡唑。通过对相应的1-丙酮基吡唑进行破坏性硝化，以良好的产率合成了所需的高能密度氧化剂3,4-二硝基-和3,5-二硝基-1-(三硝基甲基)吡唑。所有制备的化合物均通过多核NMR和IR光谱以及元素分析进行了全面表征。单晶X射线衍射研究表明其密度非常高。还进行了撞击感度测试和热稳定性测量。所有吡唑的计算生成热均为正值，并表现出有前景的能量性能，其性能范围与1,3,5-三硝基全氢-1,3,5-三嗪和季戊四醇四硝酸酯相当。新型吡唑具有正氧平衡，是新型环境友好型含能材料的有前景的候选物。
