Energetic Multifunctionalized Nitraminopyrazoles and Their Ionic Derivatives: Ternary Hydrogen-Bond Induced High Energy Density Materials

Diverse
functionalization was introduced into the pyrazole framework
giving rise to a new family of ternary hydrogen-bond induced high
energy density materials. By incorporating extended cationic interactions,
nitramine-based ionic derivatives exhibit good energetic performance
and enhanced molecular stability. Performance parameters including
heats of formation and detonation properties were calculated by using Gaussian 03 and EXPLO5 v6.01 programs,
respectively. It is noteworthy to find that 5-nitramino-3,4-dinitropyrazole, 4, has a remarkable measured density of 1.97 g cm–3 at 298 K, which is consistent with its crystal density (2.032 g
cm–3, 150 K), and ranks highest among azole-based
CHNO compounds. Energetic evaluation indicates that, in addition to
the molecular compound 4, some ionic derivatives, 9, 11, 12, 17, 19, and 22, also have high densities (1.83–1.97
g cm–3), excellent detonation pressures and velocities
(P, 35.6–41.6 GPa; vD, 8880–9430 m s–1), as well as acceptable
impact and friction sensitivities (IS, 4–30 J; FS, 40–240
N). These attractive features highlight the application potential
of nitramino hydrogen-bonded interactions in the design of advanced
energetic materials.