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Highly Dense Nitranilates‐Containing Nitrogen‐Rich Cations
Author(s) -
Huang Yangen,
Gao Haixiang,
Twamley Brendan,
Shreeve Jean'ne M.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801976
Subject(s) - detonation , halide , chemistry , nitrogen , ion , yield (engineering) , elemental analysis , inorganic chemistry , salt metathesis reaction , metathesis , analytical chemistry (journal) , crystallography , materials science , explosive material , organic chemistry , polymer , metallurgy , polymerization
High density energetic salts containing nitrogen‐rich cations and the nitranilic anion were readily synthesized in high yield by metathesis reactions of sodium nitranilate 2 and an appropriate halide. All of the new compounds were fully characterized by elemental, spectral (IR, 1 H, 13 C NMR), and thermal (DSC) analyses. The structure of hydrazinium nitranilate ( 4 ) was also determined by single‐crystal X‐ray analysis. The high symmetry and oxygen content of the anion give these salts extensive hydrogen bonding capability which further results in the high densities, low water solubilities, and high thermal stabilities ( T d > 200 °C) of these compounds. Theoretical performance calculations were carried out by using Gaussian 03 and Cheetah 5.0. The calculated detonation pressures ( P ) for these new salts fall between 17.5 GPa ( 10 ) and 31.7 GPa ( 4 ), and the detonation velocities ( νD ) range between 7022 m s −1 ( 13 ) and 8638 m s −1 ( 4 ).