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New Energetic Materials featuring Tetrazoles and Nitramines – Synthesis, Characterization and Properties
Author(s) -
Fischer Niko,
Karaghiosoff Konstantin,
Klapötke Thomas M.,
Stierstorfer Jörg
Publication year - 2010
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200900521
Subject(s) - detonation velocity , chemistry , nitro , tetrazole , detonation , standard enthalpy of formation , deprotonation , differential scanning calorimetry , medicinal chemistry , organic chemistry , explosive material , alkyl , ion , physics , thermodynamics
Abstract The alkylation of 2‐nitro‐2‐azapropyl chloride ( 2 ) and deprotonated 5‐amino‐1 H ‐tetrazole ( 3 ), 1 H ‐tetrazole ( 4 ), 5‐nitrimino‐1,4 H ‐tetrazole ( 5 ), 1‐methyl‐5‐nitrimino‐4 H ‐tetrazole ( 6 ) and 2‐methyl‐5‐nitraminotetrazole ( 7 ) afforded the products 1‐(2‐nitro‐2‐azapropyl)‐5‐aminotetrazole ( 8 ), 1‐(2‐nitro‐2‐azapropyl)‐5 H ‐tetrazole ( 9 ), 1‐(2‐nitro‐2‐azapropyl)‐5‐nitriminotetrazole · H 2 O ( 10a ), 1‐(2‐nitro‐2‐azapropyl)‐5‐nitriminotetrazole · EtOH ( 10b ) 1,5‐ bis (2‐nitro‐2‐azapropyl)‐5‐nitraminotetrazole ( 11 ), 1‐methyl‐5‐(2‐nitro‐2‐azapropyl)‐5‐nitraminotetrazole ( 12 ), 1‐methyl‐4‐(2‐nitro‐2‐azapropyl)‐5‐nitraminotetrazole ( 13 ), 1‐methyl‐5‐(2‐nitro‐2‐azapropyl)‐5‐aminotetrazole ( 14 ) and 2‐methyl‐5‐(2‐nitro‐2‐azapropyl)‐5‐nitraminotetrazole ( 15 ). In addition, the reaction of potassium 1‐methyl‐5‐nitriminotetrazolate with dimethyl sulfate was investigated yielding 1,4‐dimethyl‐5‐nitriminotetrazole ( 16 ). All products ( 8 – 16 ) were determined by low temperature single X‐ray diffraction. A comprehensive characterization and description of the chemical properties (IR, Raman, and multinuclear ( 1 H, 13 C and 15 N) NMR spectroscopy, mass spectrometry, elemental analysis and differential scanning calorimetry) is given. The heats of formation were calculated by heats of combustion measured using bomb calorimetry. With these values and the X‐ray densities, several detonation parameters (e.g. detonation pressure, detonation velocity, heat of explosion) were computed by the EXPLO5 software. In addition, the sensitivities towards impact, friction and electrical discharge were determined.