Balancing energy and stability: Synthesis, structure and performance of 3-nitro-1-(trinitromethyl)-1H-pyrazole-4-carboxylic acid and its energetic salts

3-Nitro-1-(trinitromethyl)-1 H -pyrazole-4-carboxylic acid ( 4 ) and its corresponding ammonium ( 5 ) and hydroxylammonium ( 6 ) salts were successfully synthesized from 3-amino-1 H -pyrazole-4-carbonitrile. Their structures were characterized by infrared, nuclear magnetic resonance, elemental analysis, and confirmed by single-crystal X-ray diffraction to be triclinic P 1 ¯ ( 4 ), monoclinic C 2 /c ( 5 ) and Cc ( 6 ) Space group with 2, 8, and 4 molecules per unit cell. ADCH charge analysis revealed an uneven electron density distribution across the ring system of 4 , with notably high charge density around two oxygen atoms of the carboxyl group, which facilitates hydrogen bond formation. NICS aromaticity evaluation further confirmed the strong aromatic nature of the product, with an NICS(1)zz value below -20.0 ppm. Remarkably, the hydroxylammonium salt 6 not only retains outstanding detonation properties (detonation velocity D  = 8878 m s - ¹, detonation pressure P  = 35.60 GPa) but also demonstrates superior mechanical sensitivity (impact sensitivity IS = 12 J, friction sensitivity FS = 200 N). This achieves an optimal balance between high energy and low sensitivity, meeting the design objectives for high-energy insensitive materials. The findings offer valuable insights and experimental support for the molecular design of novel energetic compounds that integrate high energy performance with robust stability.