57073-37-7Relevant articles and documents
Formamidinium Nitroformate: An Insensitive RDX Alternative
Baxter, Amanda F.,Martin, Igor,Christe, Karl O.,Haiges, Ralf
supporting information, p. 15089 - 15098 (2018/11/10)
Five nitroformate (trinitromethanide) salts featuring nitrogen-containing cations were prepared. The salts were characterized by multinuclear NMR, IR, and Raman spectroscopy, single-crystal X-ray analysis, differential thermal analysis, and friction and impact sensitivity testing. These experimental data are supplemented with thermochemical calculations using the Gaussian-4 composite method, and the performance of these energetic materials was calculated based on the Chapman-Jouguet thermodynamic detonation theory. Out of the five compounds studied by us, the formamidinium salt, [CH(NH2)2]+[C(NO2)3]-, is most interesting. Its performance matches that of RDX (research department explosive, cyclotrimethylenetrinitramine), while it is much less sensitive to impact and friction and, therefore, might be an excellent, less sensitive replacement for RDX.
Derivatives of 5-nitro-1,2,3-2H-triazole-high performance energetic materials
Zhang, Yanqiang,Parrish, Damon A.,Shreeve, Jean'Ne M.
, p. 585 - 593 (2013/07/04)
The energetic derivatives of 5-nitro-1,2,3-2H-triazole, which include 2-(methyl or amino)-4-(nitramino, azido, or nitro)-5-nitro-1,2,3-2H-triazoles, were prepared in moderate yields, and confirmed with NMR and IR spectroscopy, and elemental analysis. Their key properties, viz., melting and decomposition temperatures, densities, detonation pressures and velocities, and impact sensitivities, were measured or calculated. Among the new derivatives, 2-amino-4,5-dinitro-1,2,3-2H-triazole exhibits properties (Tm, 94 °C; Td, 190 °C; ρ, 1.83 g cm-3; P, 36.2 Gpa, vD, 8843 m s-1, IS, 24 J), comparable with RDX (T m, 205 °C; Td, 230 °C; ρ, 1.80 g cm -3; P, 35.0 Gpa, vD, 8762 m s-1, IS, 7.5 J), and may have potential as a high-performance energetic material.
α-nitration of ketones via enol silyl ethers. Radical cations as reactive intermediates in thermal and photochemical processes
Rathore, Rajendra,Kochi, Jay K.
, p. 627 - 639 (2007/10/03)
Highly colored (red) solutions of various enol silyl ethers and tetranitromethane (TNM) are readily bleached to afford good yields of α-nitro ketones in the dark at room temperature or below. Spectral analysis show the red colors to be associated with the intermolecular 1:1 electron donor-acceptor (EDA) complexes between the enol silyl ether and TNM. The formation of similar vividly colored EDA complexes with other electron acceptors (such as chloranil, tetracyanobenzene, tetracyanoquinodimethane, etc.) readily establish enol silyl ethers to be excellent electron donors. The deliberate irradiation of the diagnostic (red) charge-transfer absorption bands of the EDA complexes of enol silyl ethers and TNM at -40 °C affords directly the same α-nitro ketones, under conditions in which the thermal reaction is too slow to compete. A common pathway is discussed in which the electron transfer from the enol silyl ether (ESE) to TNM results in the radical ion triad [ESE?+, NO2?, C(NO2)3-]. A subsequent fast homolytic coupling of the cation radical of the enol silyl ether with NO2? leads to the α-nitro ketones. The use of time-resolved spectroscopy and the disparate behavior of theisomeric enol silyl ethers of α- and β-tetralones as well as of 2-methylcyclohexanone strongly support cation radicals (ESE?+) as the critical intermediate in thermal and photoinduced electron-transfer as described in Schemes 1 and 2, respectively.
