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The Many Faces of FOX‐7: A Precursor to High‐Performance Energetic Materials
Author(s) -
Gao Haixiang,
Shreeve Jean'ne M.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201501973
Subject(s) - detonation , differential scanning calorimetry , thermal stability , standard enthalpy of formation , oxygen , elemental analysis , detonation velocity , nitrogen , energetic material , chemistry , analytical chemistry (journal) , characterization (materials science) , materials science , thermodynamics , organic chemistry , nanotechnology , explosive material , physics
New derivatives of 1,1‐diamino‐2, 2‐dinitroethene (FOX‐7) are reported. These highly oxygen‐ and nitrogen‐rich compounds were fully characterized using IR and multinuclear NMR spectroscopy, elemental analysis (EA), and differential scanning calorimetry (DSC). X‐ray structure determination of ( E )‐1,2‐bis{( E )‐2‐chloro‐1‐(chloroimino)‐2,2‐dinitroethyl}diazene) ( 10 ), N1, N2‐dichloro‐1, 2‐diazenedicarboximidamide ( 11 ), and ( E , E )‐ N , N ′‐1,2‐ethanediylidenebis(2, 2‐dinitro‐2‐chloro‐ethanamine) ( 12 ) was helpful in their characterization. Heats of formation (HOF) were calculated (Gaussian 03) and combined with experimental densities to estimate the detonation velocities ( D ) and pressures ( P ) of the high‐energy‐density materials (HEDMs) (EXPLO5, v6.01). The compounds exhibit good thermal stability, high density, positive HOF, acceptable oxygen balances, and excellent detonation properties, which often are superior to that of 1,3,5‐trinitroperhydro‐1,3,5‐triazine (RDX).