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Energetic 2,2‐Dimethyltriazanium Salts: A New Family of Nitrogen‐Rich Hydrazine Derivatives
Author(s) -
Forquet Valérian,
Sabaté Carlos Miró,
Jacob Guy,
Guelou Yann,
Delalu Henri,
Darwich Chaza
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201500397
Subject(s) - chemistry , salt (chemistry) , elemental analysis , inorganic chemistry , hydrazine (antidepressant) , azide , sulfonic acid , nitrogen , thermal analysis , hydroxylamine , salt metathesis reaction , amination , chloride , nuclear chemistry , metathesis , organic chemistry , polymerization , catalysis , physics , chromatography , thermal , meteorology , polymer
Amination of 1,1‐dimethylhydrazine with NH 2 Cl or hydroxylamine‐ O ‐sulfonic acid yields 2,2‐dimethyltriazanium (DMTZ) chloride ( 3 ) and sulphate ( 4 ), respectively. The DMTZ cation was paired with the nitrogen‐rich anions 5‐aminotetrazolate ( 5 ), 5‐nitrotetrazolate ( 6 ), 5,5′‐azobistetrazolate ( 7 ), and azide ( 8 ), yielding a new family of energetic salts. The synthesis was carried out by metathesis reactions of salts 3 or 4 and a suitable silver or barium salt. To minimize the risks involved when using heavy metal salts, we used electrodialysis for the synthesis of azide 8 , which avoids the use of highly sensitive species. The DMTZ derivatives were characterized by IR and multinuclear NMR spectroscopy, elemental analysis, and X‐ray diffraction. Thermal stabilities were measured using DSC analysis and their sensitivities towards classical stimuli were determined using standard tests. Lastly, the relationship between hydrogen bonding in the solid state and sensitivity is discussed.