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Isomers of Dinitropyrazoles: Synthesis, Comparison and Tuning of their Physicochemical Properties.
ChemPlusChem ( IF 3.0 ) Pub Date : 2018-08-01 , DOI: 10.1002/cplu.201800318
Marc F Bölter 1 , Alexander Harter 1 , Thomas M Klapötke 1 , Jörg Stierstorfer 1
Affiliation  

Three isomeric dinitropyrazoles (DNPs) were synthesized starting from readily available 1H-pyrazole by slightly improved methods than described in the literature. 3,4-Dinitropyrazole (3), 1,3-dinitropyrazole (4), and 3,5-dinitropyrazole (5) were obtained and compared to each other with respect to thermal stability, crystallography, sensitivity and energetic performance. Two isomers (3 and 4) show high densities (1.79 and 1.76 g cm-3 ) and interesting thermal behavior as melt-castable materials (3: Tmelt. =71 °C, Tdec. =285 °C; 5: Tmelt. = 68 °C, Tdec. =171 °C). Furthermore, eight salts (sodium, potassium, ammonium, hydrazinium, hydroxylammonium, guanidinium, aminoguanidinium and 3,6,7-triamino-[1,2,4]triazolo[4,3-b][1,2,4]triazole (TATOT) of 3 and 5 were synthesized in order to tune performance and sensitivity values. These compounds were characterized using 1 H, 13 C, 14 N, 15 N NMR and IR spectroscopy as well as mass spectrometry, elemental analysis and thermal analysis through differential scanning calorimetry. Crystal structures of 14 compounds were obtained (3-7, 10-12 and 15-20) by low-temperature single crystal X-ray diffraction. Impact, friction and electrostatic discharge (ESD) values were also determined by standard methods. The sensitivity values range between 8.5 and 40 J for impact and 240 N and 360 N for friction and show mainly insensitive character. The energetic performances were determined using recalculated X-ray densities, heats of formation and the EXPLO5 code and support the energetic character of the title compounds. The calculated energetic performances (VD : 6245-8610 m s-1 ; pCJ : 14.1-30.8 GPa) were compared to RDX ((O2 NNCH2 )3 ).

中文翻译:

二硝基吡唑的异构体:其理化性质的合成,比较和调整。

通过比文献中描述的略有改进的方法,从容易获得的1H-吡唑开始合成了三种异构体二硝基吡唑(DNP)。得到3,4-二硝基吡唑(3),1,3-二硝基吡唑(4)和3,5-二硝基吡唑(5),并就热稳定性,晶体学,灵敏度和高能性能进行比较。两种异构体(3和4)具有高密度(1.79和1.76 g cm-3)并具有有趣的热行为,可熔融浇铸材料(3:熔融= 71°C,Tdec。= 285°C; 5:熔融= 68°C,Tdec。= 171°C)。此外,还有八种盐(钠,钾,铵,肼,羟基铵,胍盐,氨基胍和3,6,7-三氨基-[1,2,4]三唑并[4,3-b] [1,2,4]三唑合成3和5的(TOTOT),以调节性能和灵敏度值。使用1 H,13 C,14 N,15 N NMR和IR光谱以及通过差示扫描量热法进行的质谱分析,元素分析和热分析,对这些化合物进行了表征。通过低温单晶X射线衍射获得14种化合物的晶体结构(3-7、10-12和15-20)。冲击,摩擦和静电放电(ESD)值也通过标准方法确定。灵敏度值在8.5至40 J的冲击范围内,在240 N至360 N的摩擦力范围内,主要表现出不敏感的特性。使用重新计算的X射线密度,形成热和EXPLO5编码确定能量性能,并支持标题化合物的能量特征。将计算出的能量性能(VD:6245-8610 m s-1; pCJ:14.1-30.8 GPa)与RDX((O2 NNCH2)3)进行比较。
更新日期:2018-08-28
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