ANTA and its oxidation products

摘要

5-Amino-3-nitro-1H-1,2,4-triazole (ANTA) is a molecule with high stability. Aside from being an insensitive high explosive (IHE), it is also used as a synthon for other potential new IHEs. The crystal structure of ANTA was resolved by X-ray crystallography. However, when ANTA was recrystallized from 2-butanone, crystals with molecular packing characterized by 3 extended planar sheets were obtained ((beta)-ANTA). The crystal density of (beta)-ANTA is 1.73 g/cm(sup 3), which is less dense than (alpha)-ANTA ((rho) = 1.82g/cM(sup 3)). The high-nitrogen molecule, 5,5'-dinitro-3, 3'-azo-1,2,4-triazole (DNAT) was calculated to have a high density and a positive heat of formation ((Delta)H(sub f)). In an attempt to prepare DNAT, we have studied the oxidation of ANTA with different oxidizers. It was found that DNAT is the reaction product when the potassium salt of ANTA was oxidized with potassium pemanganate. However, when ANTA was oxidized with ammonium persulfate in aqueous medium, one of the reaction products obtained was the azoxy molecule of DNAT (DNAzT). We are unable to determine the crystal densities of either DNAT and DNAzT because the crystals obtained were solvated with the crystallization solvents.