Energetic Salts of Sensitive N,N'-(3,5-Dinitropyrazine-2,6-diyl)dinitramide Stabilized through Three-Dimensional Intermolecular Interactions.

N-nitration of 2,6-diamino-3,5-dinitropyrazine (ANPZ) leads to a sensitive energetic compound N,N'-(3,5-dinitropyrazine-2,6-diyl)dinitramide. This nitro(nitroamino) compound was stabilized by synthesizing energetic salts, dipotassium (3,5-dinitropyrazine-2,6-diyl)bis(nitroamide) ( 3 ) and diammonium (3,5-dinitropyrazine-2,6-diyl)bis(nitroamide) ( 4 ). Compounds 3 and 4 are fully characterized by single-crystal X-ray diffraction. Compound 3 exhibits a three-dimensional energetic metal-organic framework (3D EMOF) structure and an outstanding overall performance by combining high experimental density (2.10 g cm -3 ), good thermal stability ( T d(onset) = 220 °C), and good calculated performance of detonation ( D = 8300 m s -1 , P = 29.9 GPa). Compound 4 has acceptable thermal stability (155 °C), moderate experimental density (1.73 g cm -3 ), and good calculated performance of detonation ( D = 8624 m s -1 , P = 30.8 GPa). The sensitivities of compounds 3 and 4 toward impact and friction were determined following standard methods (BAM). The energetic character of compounds 3 and 4 was determined using red-hot needle and heated plate tests. The results highlight a 3D EMOF ( 3 ) based on a six-membered heterocycle as a potential energetic material.