Assembly of Nitrofurazan and Nitrofuroxan Frameworks for High‐Performance Energetic Materials

Ферштат, Леонид Л.; Овчинников, И. В.; Epishina, Margarita A.; Romanova, Anna A.; Лемперт, Д. Б.; Muravyev, Nikita V.; Махова, Нина Н.

doi:10.1002/cplu.201700340

Cited by 54 publications

(27 citation statements)

References 54 publications

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“…The latter obviously affects atomic QTAIM partitioning and values of atomic volumes enclosed by the isosurface of electron density which we use as the boundary condition for calculations of atomic and ionic contributions to the density of isolated species. As we already demonstrated, the presence of intramolecular noncovalent interactions can determine the crystal packing of high‐energy furoxan systems to a large extent . Therefore, it is of importance to estimate the influence of possible intramolecular noncovalent bonding in tetrazolylfuroxan anions on the contributions to crystal density.…”

Section: Resultsmentioning

confidence: 95%

“…Namely, the larger difference between the density of chemical functions in the isolated anions from DUQGUT and 8⋅ H 2 O structures is observed for the azido group and it is nearly meaningless, 0.0002 g cm −3 . Moreover, this noncovalent interaction in DUQGUT is repulsive in terms of the interacting quantum atoms approach (Figure S5) or, at least, very weak (≈1 kcal mol −1 ) according to the correlation of the interatomic surface integral of electron density and nondirectional (ellipticity of electron density at bond critical point equals 0.99), which makes it highly likely to be affected by vibrational smearing and/or supramolecular association …”

Section: Resultsmentioning

confidence: 99%

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Assembly of Tetrazolylfuroxan Organic Salts: Multipurpose Green Energetic Materials with High Enthalpies of Formation and Excellent Detonation Performance

Larin

Muravyev

Пивкина

et al. 2019

Chemistry A European J

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A series of highly energetic organic salts comprising a tetrazolylfuroxan anion, explosophoric azido or azo functionalities, and nitrogen‐rich cations were synthesized by simple, efficient, and scalable chemical routes. These energetic materials were fully characterized by IR and multinuclear NMR (1H, 13C, 14N, 15N) spectroscopy, elemental analysis, and differential scanning calorimetry (DSC). Additionally, the structure of an energetic salt consisting of an azidotetrazolylfuroxan anion and a 3,6,7‐triamino‐7H‐[1,2,4]triazolo[4,3‐b][1,2,4]triazolium cation was confirmed by single‐crystal X‐ray diffraction. The synthesized compounds exhibit good experimental densities (1.57–1.71 g cm−3), very high enthalpies of formation (818–1363 kJ mol−1), and, as a result, excellent detonation performance (detonation velocities 7.54–8.26 kms−1 and detonation pressures 23.4–29.3 GPa). Most of the synthesized energetic salts have moderate sensitivity toward impact and friction, which makes them promising candidates for a variety of energetic applications. At the same time, three compounds have impact sensitivity on the primary explosives level (1.5–2.7 J). These results along with high detonation parameters and high nitrogen contents (66.0–70.2 %) indicate that these three compounds may serve as potential environmentally friendly alternatives to lead‐based primary explosives.

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Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

Assembly of Tetrazolylfuroxan Organic Salts: Multipurpose Green Energetic Materials with High Enthalpies of Formation and Excellent Detonation Performance

Larin

Muravyev

Пивкина

et al. 2019

Chemistry A European J

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“…Our research team has a great experience in the synthesis and reactivity of furoxans [10][11][12][13][14]. Therefore, to prepare the target compound 1, we have used the nitration of the previously synthesized [6] 4,4 -diamino-3,3 -diazenofuroxan 2.…”

Section: Resultsmentioning

confidence: 99%

3,3′-(Diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide]

Larin

Овчинников

Ферштат

et al. 2018

Molbank

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The nitramino derivatives of furoxans are of specific interest as precursors for the preparation of high energy salts with nitrogen-rich cations. In this communication, the 3,3-(diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide] was prepared via nitration of available 4,4-diamino-3,3-diazenofuroxan; the best yield of the target compound was achieved under the action of nitrating system HNO 3 /(CF 3 CO) 2 O in molar ratio 15:3 in CCl 4 at −5 • C. The structure of 3,3-(diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide] was confirmed by means of 1 H, 13 C, 14 N-NMR, IR spectroscopy and high resolution mass spectra (HRMS).

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“…The nitro and amino derivatives of furazans and furoxans have drawn much interest of chemists as a field of compounds with presumably high energy content . The polycyclic compounds composed of few fused furazan and/or furoxan cycles are attractive especially for practical use, since some of them demonstrate exceptionally high explosion characteristics while being suitable enough with regard to their thermal stability.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure Prediction of Bifurazano[3,4‐b:3′,4′‐f][3′′,4′′‐d](BFFO) in the Experimentally Known Monohydrated and Proposed Anhydrous Forms

Khakimov

Dzyabchenko

Pivina

2019

Propellants Explo Pyrotec

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Bifurazano[3, [3'',4''-d]xacycloheptatriene (BFFO, C 6 N 6 O 5 ) is perspective high-energy-density compound. The crystal structure was previously determined for its monohydrate (space group P2 1 /c, Z = 4), while it remains unknown for pure BFFO being of primary interest. Herein a theoretical crystal structure prediction of BFFO in both monohydrated and the proposed anhydrous forms is performed. The Coulomb energy was calculated with advanced point charge models reproducing with high accuracy electrostatic potentials of the BFFO and water molecules. The van der Waals energy was calculated with empirical atom-atom potentials. The global search for energy minima involved enumeration of 35 most likely organ-ic structural classes with one and two independent molecules (Z = 1 and 2). A characteristic feature of the energy landscape of an anhydrous BFFO is that the energies of the deepest minima differ very little. However the structures in the space group Pbca, Z = 8 and P2 1 /c, Z = 8 were found the most energetically preferable. The common feature of predicted BFFO structures is the presence of herring-bone packing motifs instead of stacking configurations. The detonation pressure and velocity of pure BFFO crystal (presumably a high-energy explosive) are estimated from the predicted density; the latter occurs to be lower than density of the monohydrate form.

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Assembly of Nitrofurazan and Nitrofuroxan Frameworks for High‐Performance Energetic Materials

Cited by 54 publications

References 54 publications

Assembly of Tetrazolylfuroxan Organic Salts: Multipurpose Green Energetic Materials with High Enthalpies of Formation and Excellent Detonation Performance

Assembly of Tetrazolylfuroxan Organic Salts: Multipurpose Green Energetic Materials with High Enthalpies of Formation and Excellent Detonation Performance

3,3′-(Diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide]

Crystal Structure Prediction of Bifurazano[3,4‐b:3′,4′‐f][3′′,4′′‐d](BFFO) in the Experimentally Known Monohydrated and Proposed Anhydrous Forms

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