Aminoacetonitrile as precursor for nitrogen rich stable and insensitive asymmetric N-methylene-C linked tetrazole-based energetic compounds

Reaction of aminoacetonitrile with cyanogen azide resulted in acetonitrile derivative of amino(tetrazole), 1, which on further reaction with sodium azide in the presence of ammonium chloride resulted in compound 2 with N-methylene-C bridged tetrazole and amino-tetrazole moieties. Reaction of 2 with 100% nitric acid resulted in N-(1-((1H-tetrazol-5-yl) methyl)-1H-tetrazol-5(4H)-ylidene) nitramide (4) having N-methylene-C bridged nitroimino-tetrazole and tetrazole moieties. Various energetic salts based on these three types of tetrazole derivatives (tetrazole, amino-tetrazole and nitroimino-tetrazole) in 2 and 4 were obtained. All the compounds were thoroughly characterized by IR, NMR [H-1, C-13{H-1}, N-15], elemental analysis, and differential scanning calorimetry (DSC). Some of them were also structurally characterized with single-crystal X-ray diffraction studies. Heats of formation and detonation performances for all the energetic compounds were calculated using Gaussian 03 and EXPLO5 v6.01 programs, respectively.