Jean'ne M. Shreeve - Idaho, Moscow, Idaho orcid.org/0000-0001-8622-4897; uidaho.edu; Fax: (+1)

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) com-pound was stabilized by synthesizing energetic salts, dipotassium (3,5-dinitropyrazine-2,6-diyl)bis(nitroamide) (3) and diammo-nium (3,5-dinitropyrazine-2,6-diyl)bis(nitroamide) (4). Com-pounds 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 out-standing overall performance by combining high experimental density (2.10 g cm-3), good thermal stability (Td(onset) = 220 degrees C), and good calculated performance of detonation (D = 8300 m s-1, P = 29.9 GPa). Compound 4 has acceptable thermal stability (155 degrees 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.

Automated summary

The N-nitration of 2,6-diamino-3,5-dinitropyrazine (ANPZ) resulted in the synthesis of a sensitive and energetic compound, N,N'-(3,5-dinitropyrazine-2,6-diyl)dinitramide. This compound was further stabilized by synthesizing dipotassium and diammonium salts. Compound 3 exhibited a three-dimensional energetic metal-organic framework (3D EMOF) structure with outstanding overall performance, while compound 4 had acceptable thermal stability and good calculated performance of detonation.