Synthesis and characterization of 1,4-dimethyl-5-aminotetrazolium 5-nitrotetrazolate

1,4-Dimethyl-5-aminotetrazolium 5-nitrotetrazolate (2) was synthesized in high yield from 1,4-dimethyl-5-aminotetrazolium iodide (1) and silver 5-nitrotetrazolate. Both new compounds (1, 2) were characterized using vibrational (IR and Raman) and multinuclear NMR spectroscopy (H-1, C-13, N-14, N-15), elemental analysis and single crystal X-ray diffraction. 1,4-Dimethyl-5-aminotetrazolium 5-nitrotetrazolate (2) represents the first example of an energetic material which contains both a tetrazole based cation and anion. Compound 2 is hydrolytically stable with a high melting point of 190 degrees C (decomposition). The impact sensitivity of compound 2 is very low (30 J), it is not sensitive towards friction (> 360 N). The molecular structure of 1,4-dimethyl-5-aminotetrazolium iodide (1) in the crystalline state was determined by X-ray crystallography: orthorhombic, F-ddd, a=1.3718(1) nm, b= 1.4486(1) nm, c=1.6281.(1) nm, V=3.2354(5) nm(3), Z=16, rho= 1.979 g cm(-1), R-1=0.0169 (F > 4 sigma(F)), wR(2) (all data) =0.0352. The molecular structure of 1,4-dimethyl-5-aminotetrazolium 5-nitrotetrazolate (2) in the crystalline state was also determined by X-ray crystallography: orthorhombic, P 2(1)2(1)2(1), a=0.5709(1) nm, b=1.2866(2) nm, c=1.3328(2) nm, V=0.9789(3) nm(3), Z=4, rho= 1.548 g cm(-1), R-1 = 0.0389 (F > 4 sigma (F)), wR(2) (all data) =0.0973.