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4‐(1‐Amino‐5‐aminotetrazolyl)methyleneimino‐3‐methylfuroxan and Its Derivatives: Synthesis, Characterization, and Energetic Properties
Author(s) -
Tang Yongxing,
Yang Hongwei,
Shen Jianhua,
Wu Bo,
Ju Xuehai,
Lu Chunxu,
Cheng Guangbin
Publication year - 2014
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201301363
Subject(s) - chemistry , nitration , yield (engineering) , elemental analysis , raman spectroscopy , 1,2,4 triazole , detonation , nitrogen , infrared spectroscopy , single crystal , crystal structure , energetic material , crystallography , organic chemistry , explosive material , materials science , physics , optics , metallurgy
The condensation reaction of 4‐formyl‐3‐methylfuroxan with 1,5‐diaminotetrazole led to 4‐(1‐amino‐5‐aminotetrazolyl)methyleneimino‐3‐methylfuroxan ( 1 ) in high yield. Its structure was confirmed by an X‐ray diffraction study. 4‐(1‐Amino‐5‐nitriminotetrazolyl)methyleneimino‐3‐methylfuroxan ( 2 ) was obtained through the nitration of 1 with 100 % HNO 3 . The nitrogen‐rich salts of 2 with bases such as 1‐amino‐1,2,3‐triazole ( 3 ), 4‐amino‐1,2,4‐triazole ( 4 ), and 3‐amino‐1,2,4‐triazole ( 5 ) were synthesized and characterized by IR, Raman, and NMR spectroscopy and elemental analysis. In addition, the structures of 2 , 4 , and 5 were further confirmed by single‐crystal X‐ray diffraction analyses. Compound 5 decomposes at 183 °C, whereas 3 and 4 are less stable and decompose at 139 and 164 °C, respectively. The heats of formation, detonation parameters, and impact sensitivity of 1 – 5 were investigated by theoretical and experimental methods.