Crystal structure of 4,4″-dinitro-[3,3′,4′,3″]-tris-[1,2,5]-oxadiazole

Алдошин, С. М.; Алиев, З. Г.; Astrat'ev, A. A.; Goncharov, T. K.; Дашко, Д. В.; Milekhin, Yu. M.; Степанов, А. И.; Shishov, N. I.

doi:10.1134/s0022476613020285

Cited by 9 publications

(7 citation statements)

References 5 publications

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“…In general, all bond lengths and angles were observed as expected and are comparable to similar crystal structures of furazanes, [9] furoxanes, [10] and tetrazole-oxides [11] in literature. Compound 3 crystallizes in the monoclinic space group C2/c with four molecules in the unit cell.…”

Section: Crystal Structuressupporting

confidence: 82%

Energetic alliance of tetrazole-1-oxides and 1,2,5-oxadiazoles

et al. 2015

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ARTICLE This journal isThe connection of highly endothermic heterocycles with high nitrogen but also oxygen content is a recent trend in the development of new energetic materials in order to increase densities and stabilities. Bis(1-hydroxytetrazolyl)furazane (9) and bis(1-hydroxytetrazolyl)furoxane (10) were synthesized for the first time from dicyanofurazane and dicyanofuroxane, respectively. Several nitrogen-rich (e.g. ammonium and hydroxylammonium) and metal salts thereof were prepared. Most compounds were characterized by single crystal X-ray diffraction. In addition all compounds were analyzed by vibrational spectroscopy (IR and Raman), multinuclear NMR spectroscopy, elemental analysis and DSC measurements. The heats of formation of 4, 5, 15-16, 20 and 24 were calculated using the atomization method based on CBS-4M enthalpies. With these values and the experimental (X-ray) densities several detonation parameters such as the detonation pressure, velocity, energy and temperature were computed using the EXPLO5 code (V.5.05). In addition, the sensitivities towards impact, friction and electrical discharge were tested using the BAM drop hammer and friction tester as well as a small scale electrical discharge device.

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Section: Crystal Structuressupporting

confidence: 82%

Energetic alliance of tetrazole-1-oxides and 1,2,5-oxadiazoles

et al. 2015

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“…The final one is of the stacking between two furazan rings. As illustrated in Figure 2d, in the furazan rings of NTF, 65 DNAzF, 66 and CFNF, 67 lone pairs exist around both the N and O atoms and particularly on the acyloxy (NO) of DNAzF; therefore, they serve as n; meanwhile, the furazan rings are generally electron-poor and serve as the positively charged π. These electricity of n and π that roots for the electrostatic attraction will be clarified by the following discussion of ESP.…”

Section: Resultsmentioning

confidence: 99%

n−π Stacking in Energetic Crystals

Gou

Zhang

2022

Crystal Growth & Design

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n−π stacking refers to the molecular stacking through the lone-pair electron (n)-π-structure interaction. As an important stacking mode supplementary to hydrogen bonding (HB) and π–π stacking, which are usually dominant in the intermolecular interaction, it has generally been ignored in energetic crystals. This work extracts typical n−π stacked energetic single-component crystals and cocrystals from CSD and categorizes them into three forms, including the contacts of the NO2 benzene ring, NO2 heterocycle, and furazan ring–furazan ring. The n−π stacking in energetic crystals has the nature of weak electrostatic attraction because each n−π couple always possesses a weakly positively charged π and a weakly negatively charged n. This attraction ranges from 6.3 to 20.0 kJ/mol in energy and is generally weaker than intermolecular HB and π–π stacking. The n−π stacking exhibits a mode of T-shape and can hardly occur alone for planar molecules with strong HB acceptors and donors. Hopefully, this work is expected to enrich and perfect the knowledge of the intermolecular interactions in energetic crystals and pave the way for a comprehensive understanding of molecular stacking therein.

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“…A number of attempts has been made to overcome these drawback, the first way was to form eutectic explosives with other explosives, and the second way was to modify its structure to develop new derivatives. The latter solution has recently attracted much attention, and two low melting-point explosives BNTF (84 8C) and ANTF (100 8C) were synthesized [8][9][10][11]. BNTF and ANTF have recently been suggested to be used as a novel carrier of melt-cast explosives because of their low melting point, good stability, detonation performance, and low sensitivity [10].…”

Section: Introductionmentioning

confidence: 99%

“…Secondly,i th as ah igher impact sensitivity (IS) than other melt-cast explosives such as TNT,w hich prevented it from aw ide range of applications [6,7].A number of attempts has been made to overcomet hese drawback, the first way was to form eutectic explosives with other explosives, and the second way was to modify its structure to develop new derivatives. The latter solution has recently attracted much attention, and two low melting-point explosives BNTF (84 8C) and ANTF (100 8C) were synthesized [8][9][10][11].BNTF and ANTF have recently been suggested to be used as an ovel carrier of melt-cast explosives because of their low melting point, good stability,d etonation performance, and low sensitivity [ 10].However,i nvestigations on the thermal decomposition and crystal structure of ANTF have not beenr eported to date, except for BNTF.I nt his work, an improved synthesis (Scheme 1), crystal structure, and thermal behavior of ANTF are reported.…”

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confidence: 99%

Synthesis, Crystal Structure, and Thermal Behavior of 3‐(4‐Aminofurazan‐3‐yl)‐4‐(4‐nitrofurazan‐3‐yl)furazan (ANTF)

Liang

et al. 2016

Propellants Explo Pyrotec

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The energetic material 3‐(4‐aminofurazan‐3‐yl)‐4‐(4‐nitrofurazan‐3‐yl)furazan (ANTF) with low melting‐point was synthesized by means of an improved oxidation reaction from 3,4‐bis(4′‐aminofurazano‐3′‐yl)furazan. The structure of ANTF was confirmed by 13C NMR spectroscopy, mass spectrometry, and the crystal structure was determined by X‐ray diffraction. ANTF crystallized in monoclinic system P21/c, with a crystal density of 1.785 g cm−3 and crystal parameters a=6.6226(9) Å, b=26.294(2) Å, c=6.5394(8) Å, β=119.545(17)°, V=0.9907(2) nm3, Z=4, μ=0.157 mm−1, F(000)=536. The thermal stability and non‐isothermal kinetics of ANTF were studied by differential scanning calorimetry (DSC) with heating rates of 2.5, 5, 10, and 20 K min−1. The apparent activation energy (Ea) of ANTF calculated by Kissinger's equation and Ozawa's equation were 115.9 kJ mol−1 and 112.6 kJ mol−1, respectively, with the pre‐exponential factor lnA=21.7 s−1. ANTF is a potential candidate for the melt‐cast explosive with good thermal stability and detonation performance.

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Crystal structure of 4,4″-dinitro-[3,3′,4′,3″]-tris-[1,2,5]-oxadiazole

Cited by 9 publications

References 5 publications

Energetic alliance of tetrazole-1-oxides and 1,2,5-oxadiazoles

Energetic alliance of tetrazole-1-oxides and 1,2,5-oxadiazoles

n−π Stacking in Energetic Crystals

Synthesis, Crystal Structure, and Thermal Behavior of 3‐(4‐Aminofurazan‐3‐yl)‐4‐(4‐nitrofurazan‐3‐yl)furazan (ANTF)

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