517-25-9Relevant academic research and scientific papers
Trinitromethane
Schoedel, Holger,Dienelt, Ruediger,Bock, Hans
, p. 1790 - 1792 (1994)
The structure of cubic trinitromethane, CHN3O6, has been determined at 200 K.Warning: a severe explosion has been reported during the preparation of a sodium trinitromethanide salt.
THE MECHANISM OF AROMATIC NITRATION BY TETRANITROMETHANE
Isaacs, Neil S.,Abed, Obaid Hassan
, p. 2799 - 2802 (1982)
Aromatic nitrations by tetranitromethane are shown to be photochemically initiated and are believed to proceed via trinitromethyl nitrite.
Formamidinium Nitroformate: An Insensitive RDX Alternative
Baxter, Amanda F.,Martin, Igor,Christe, Karl O.,Haiges, Ralf
, p. 15089 - 15098 (2018)
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.
Synthesis of Neutral and Charged Trinitromethyl Borohydrides and Their Complexes
Shitov,Tartakovskii,Ioffe
, p. 1647 - 1657 (2015/02/05)
We propose several simple and effective methods for the synthesis of previously unknown trinitromethyl borohydrides and their complexes with simple cyclic ethers and aromatic nitrogen- containing heterocycles, whereas acyclic ethers did not form such complexes. The data from physicochemical investigations showed that these unique compounds contain directly linked oxidizing and reducing fragments. Some transformations of trinitromethylborane complexes were demonstrated, which can occur by cleavage of all types of bonds formed by boron atom in the starting compounds.
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.
Photochemical Nitration by Tetranitromethane. VIII. Isolation, X-Ray Structural Analysis and Chemical Properties of a Vicinal Nitro/trinitromethyl Adduct from Fluoranthene
Eberson, Lennart,Hartshorn, Michael P.,Radner, Finn,Robinson, Ward
, p. 410 - 415 (2007/10/02)
The photolysis of a dichloromethane solution of fluoranthene and tetranitromethane by light with cut-off at λ less than 435 nm gave a mixture of nitro/trinitromethyl adducts (ca. 10percent) and nitrofluoranthenes (ca. 60percent).One of the adducts could be isolated and proved to be a vicinal one trans-2-nitro-3-trinitromethyl-2,3-dihydrofluoranthene (1), as demonstrated by in X-ray crystallographic analysis.Adducts were formed in acetonitrile too, but the adduct yield was smaller.Adduct 1 was stable for many days in dichloromethane but slowly (τ1/2 about 19 h) eliminated nitroform to give 2-nitrofluoranthene in acetonitrile, whereas added hindered or unhindered bases strongly accelerated the reaction in both dichloromethane and acetonitrile.Under GLC condition 1 analyzed as 2-nitrofluoranthene.The spin adduct of trinitromethyl radical and α-phenyl-N-tert-butylnitrone (PBN) was formed and detected by EPR spectroscopy in low concentration and persisted for a long time when 1 and PBN were kept in dichloromethane solution.
The Addition-Elimination Mechanism in the Photonitration of Naphthalene by Tetranitromethane
Eberson, Lennart,Hartshorn, Michael P.,Radner, Finn,Robinson, Ward T.
, p. 566 - 567 (2007/10/02)
By the isolation and kinetic studies of an adduct (cis-1,4-dihydro-1-nitro-4-trinitromethylnaphthalene) from the photolysis of naphthalene-tetranitromethane in dichloromethane or acetonitrile, it is shown that the route to nitro substitution products proceeds via addition-elimination, the latter step being either thermal or base-catalysed.
REACTION OF α-POLYNITROALKYL DERIVATIVES OF SULFUR AND SELENUM WITH HYDROGEN HALIDES AND HALIDE IONS
Erashko, V. I.,Baryshnikov, A. T.,Zubanova, N. I.,Tishaninova, A. A.
, p. 1939 - 1944 (2007/10/02)
Hydrogen halides ( HCl and HF) react with α-polynitroalkylsulfides and α-polynitroalkylselenides as elctrophilic or as nucleophilic reagents depending on the conditions, forming accordingly products of electrophilic or nucleophilic substitution at the α-carbon atom.In contrast to this, halogen ions (Cl-, F-) always bond to the α-carbon.The use of dipolar aprotic solvents ad activators ( Lewis acids or strong mineral acids) facilitates the formation of products of nucleophilic substitution at the α-carbon.
CHEMICAL GENERATION OF TRINITROMETHYL RADICALS IN THE REACTION OF XENON DIFLUORIDE WITH THE NITROFORM ANION
Tselinskii, I. V.,Mel'nikov, A. A.,Trubitsin, A. E.
, p. 619 - 622 (2007/10/02)
In the reaction between the trinitromethane potassium salt and xenon difluoride in acetonitrile in the presence of benzene and THF the trinitromethyl derivatives of benzene and THF are formed in addition to the fluorination products.This indicates that the reaction takes place through the formation of trinitromethyl radicals.
