2-Nitroguanidine Derivatives: V. Synthesis and Structure of 3,5-Bis(nitroamino)-1,2,4-triazole Salts. Acid–Base Properties of 3,5-Bis(nitroamino)-1,2,4-triazole

Abstract

Heterocyclization of hydrazine-1,2-bis(N 2-nitrocarboximidamide) and salts derived therefrom provides a procedure for the synthesis of 3,5-bis(nitroamino)-1,2,4-triazole salts. The presence of two acceptor nitroamino groups conjugated with the triazole ring considerably enhances the acidity of 3,5-bis(nitroamino)-1,2,4-triazole (pK a1= –2.0, pKa2 = 4.8, pKa3 = 10.6) as compared to mononitroaminotriazole, so that formation of salts with the corresponding dianion becomes possible.