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Aromatic Nucleophilic Substitution of FOX‐7: Synthesis and Properties of 1‐Amino‐1‐Picrylamino‐2,2‐Dinitroethylene (APDE) and Its Potassium Salt [K(APDE)]
Author(s) -
Li Chuping,
Feng Zhicun,
Wang Hao,
Zhou Tianhong,
Li Yanan,
Xu Kangzhen
Publication year - 2019
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201900236
Subject(s) - detonation , chemistry , potassium , nucleophilic substitution , thermal decomposition , thermal stability , detonation velocity , explosive material , nucleophile , salt (chemistry) , nucleophilic aromatic substitution , stacking , decomposition , chloride , trinitrotoluene , nuclear magnetic resonance spectroscopy , crystallography , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Two energetic compounds, 1‐amino‐1‐picrylamino‐2,2‐dinitroethylene (APDE) and its potassium salt [K(APDE)] were synthesized through an aromatic nucleophilic substitution reaction between FOX‐7 and picryl chloride. APDE and K(APDE) were characterized by elemental analysis, IR, NMR spectroscopy, and X‐ray diffraction. APDE has a 3D wavy layered stacking structure similar to FOX‐7. K(APDE) (peak temperature ( T ip )=185.6 °C and impact sensitivity (IS)=19.6 J) presents better stability than APDE ( t ap =133.3 °C and IS=15.7 J). The reasons why the stability of APDE is lower than that of FOX‐7 and picryl chloride are analyzed. The detonation velocity ( D ) and detonation pressure ( P ) of APDE (8.36 km s −1 and 31.3 Gpa) are close to those of FOX‐7 and RDX. The thermal decomposition of K(APDE) is very violent, and its detonation performance ( D =9.14 km s −1 and P =38.6 Gpa) is comparable to that of HMX, indicating that K(APDE) has good potential to be a high explosive.