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Synthesis and Characterization of a New Class of Energetic Compounds – Ammonium Nitriminotetrazolates
Author(s) -
Klapötke Thomas M.,
Laub Hans A.,
Stierstorfer Jörg
Publication year - 2008
Publication title -
propellants, explosives, pyrotechnics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.56
H-Index - 65
eISSN - 1521-4087
pISSN - 0721-3115
DOI - 10.1002/prep.200700226
Subject(s) - monoclinic crystal system , detonation velocity , detonation , raman spectroscopy , differential scanning calorimetry , deprotonation , chemistry , calorimetry , infrared spectroscopy , analytical chemistry (journal) , spectroscopy , energetic material , standard enthalpy of formation , crystallography , nuclear chemistry , crystal structure , organic chemistry , thermodynamics , ion , physics , quantum mechanics , optics , explosive material
1‐Methyl‐5‐nitriminotetrazole ( 1 ) and 2‐methyl‐5‐nitraminotetrazole ( 2 ) obtained by nitration of 1‐methyl‐5‐aminotetrazole ( 3 ) and 2‐methyl‐5‐aminotetrazole ( 4 ) were deprotonated using aqueous ammonia solution yielding the energetic compounds, ammonium 1‐methyl‐5‐nitriminotetrazolate ( 5 ) and ammonium 2‐methyl‐5‐nitriminotetrazolate ( 6 ). The nitrogen‐rich salts were tested and characterized comprehensively using vibrational spectroscopy (Infrared (IR) and Raman), multinuclear ( 1 H, 13 C, 14 N, and 15 N) NMR spectroscopy, and elemental analysis. The molecular structures in the crystalline state were determined using low temperature single crystal X‐ray diffraction. The thermal behavior and the decompositions were investigated using differential scanning calorimetry (DSC) and gas IR spectroscopy. The heats of formation were calculated using bomb calorimetric measurements. In addition, the relevant detonation parameters, like the detonation pressure and velocity of detonation were calculated using the software EXPLO5 outperforming the values of TNT. Last but not least the sensitivities were determined using BAM methods showing moderate values against impact and friction (drophammer and friction tester) and the long‐term stabilities were tested using Flexy Thermal safety calorimetry (TSC). X‐ray crystallography: 5 : monoclinic, P 2 1 / c, a =370.06(2) pm, b =2079.06(9) pm, c =859.69(5) pm, β =99.120(5)°, V=65306(6) pm 3 , Z=4, ρ calc =1.639 g cm −3 ; 6 : monoclinic, P 2 1 , a =365.39(2) pm, b= 788.82(5) pm, c =1124.95(7) pm, β =91.818(6), V =32408(3) pm 3 , Z =2, ρ calc =1.651 g cm −3 .