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：

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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。