Energetic C-trinitromethyl-substituted pyrazoles: synthesis and characterization

A new family of C-trinitromethyl-substituted pyrazoles was designed and obtained in good yields by the reaction of N2O4 with the pyrazolecarbaldehyde oxime followed by further N-nitration and C-nitration. All of the new compounds were fully characterized by IR and NMR spectroscopy, elemental analysi...

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Published inDalton transactions : an international journal of inorganic chemistry Vol. 48; no. 4; pp. 1524 - 1529
Main Authors Zhang, Yiying, Li, Yanan, Hu, Jianjian, Ge, Zhongxue, Sun, Chenghui, Pang, Siping
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 22.01.2019
Subjects
Chemical analysis
Crystallography
Detonation
Enthalpy
Flux density
HMX
Infrared spectroscopy
Nitration
Nitrogen tetroxide
NMR spectroscopy
Pyrazole
Specific impulse
Substitutes
Thermal stability
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Summary:A new family of C-trinitromethyl-substituted pyrazoles was designed and obtained in good yields by the reaction of N2O4 with the pyrazolecarbaldehyde oxime followed by further N-nitration and C-nitration. All of the new compounds were fully characterized by IR and NMR spectroscopy, elemental analysis and differential scanning calorimetry (DSC). Compounds 2 and 3 were further confirmed by X-ray crystallography. These pyrazole derivatives have good densities, positive enthalpies of formation and acceptable sensitivity values. Theoretical calculations carried out using Gaussian 03 and EXPLO5 program demonstrate good to excellent detonation velocities and pressures in the range of ADN and HMX. Compound 3 exhibiting a positive oxygen balance, high specific impulse and moderate thermal stability is a promising high energy density oxidizer.
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ISSN:1477-9226
1477-9234
DOI:10.1039/c8dt04712j