Formation of trinitromethyl functionalized 1,2,4-triazole-based energetic ionic salts and a zwitterionic salt directed by an intermolecular and intramolecular metathesis strategy

Abstract

Ionic salts of 5,5′-bis(trinitromethyl)-3,3′-bi-1H-1,2,4-triazole and an unexpected energetic zwitterion 5-diazonium-3-trinitromethyl-1,2,4-triazolate were synthesized via an intermolecular and intramolecular metathesis strategy. Compared with its ammonium (6), hydrazinium (7) and hydroxylammonium (8) salts, 5,5′-bis(trinitromethyl)-3,3′-bi-1H-1,2,4-triazole (5) exhibits lower sensitivities (IS: 22.5 J and FS: 252 N). It is worth noting that energetic salt 8 exhibits a high density of 1.97 g cm⁻³ and an excellent calculated detonation velocity of 9468 m s⁻¹, and that the energetic zwitterion 5-diazonium-3-trinitromethyl-1,2,4-triazolate (14) exhibits a high density of 1.893 g cm⁻³ and an excellent calculated detonation velocity of 9317 m s⁻¹, which are both superior to that of HMX (9254 m s⁻¹).