Synthesis, Characterization and Properties of Ureido‐Furazan Derivatives

Hermann, T. S.; Klapötke, Thomas M.; Krumm, Burkhard; Stierstorfer, Jörg

doi:10.1002/jhet.3109

Cited by 21 publications

(7 citation statements)

References 42 publications

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“…The five most common explosives tested, and the number of observations per explosive, are given in Table . Unless otherwise noted, we use log E 50 to represent sensitivity, where “log” is the base-10 logarithm, as in Kamlet, Nefati et al, and Wang et al The main source of data was legacy LANL tests; however, many of the data were obtained from the published scientific literature. ,− …”

Section: Datamentioning

confidence: 99%

Chemical Descriptors for a Large-Scale Study on Drop-Weight Impact Sensitivity of High Explosives

Marrs

Davis

Burch

et al. 2023

J. Chem. Inf. Model.

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The drop-weight impact test is an experiment that has been used for nearly 80 years to evaluate handling sensitivity of high explosives. Although the results of this test are known to have large statistical uncertainties, it is one of the most common tests due to its accessibility and modest material requirements. In this paper, we compile a large data set of drop-weight impact sensitivity test results (mainly performed at Los Alamos National Laboratory), along with a compendium of molecular and chemical descriptors for the explosives under test. These data consist of over 500 unique explosives, over 1000 repeat tests, and over 100 descriptors, for a total of about 1500 observations. We use random forest methods to estimate a model of explosive handling sensitivity as a function of chemical and molecular properties of the explosives under test. Our model predicts well across a wide range of explosive types, spanning a broad range of explosive performance and sensitivity. We find that properties related to explosive performance, such as heat of explosion, oxygen balance, and functional group, are highly predictive of explosive handling sensitivity. Yet, models that omit many of these properties still perform well. Our results suggest that there is not one or even several factors that explain explosive handling sensitivity, but that there are many complex, interrelated effects at play.

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Section: Datamentioning

confidence: 99%

Chemical Descriptors for a Large-Scale Study on Drop-Weight Impact Sensitivity of High Explosives

Marrs

Davis

Burch

et al. 2023

J. Chem. Inf. Model.

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“…To avoid the drawback above, an effective strategy is to introduce nitrogen-rich backbones (such as, triazole, tetrazole, and oxadiazole) into the design of HEDMs owing to their high heats of formation. − With our continuing interest, herein we report the synthesis, structure, and energetic performance of 1,2-bis(3-(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5-yl)diazene ( 5 ), which shows the face-to-face crystal stacking and a relatively high enthalpy. Furthermore, quantum chemical calculations are employed to better understand the intrinsic structure–property relationship.…”

Section: Introductionmentioning

confidence: 99%

C₈N₁₂O₈: A Promising Insensitive High-Energy-Density Material

Wang

Shao

2018

Crystal Growth & Design

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It is desirable to consider crystal engineering in the research of energetic materials. Herein, we report the synthesis, structure, and energetic properties of a promising explosive, 1,2-bis(3-(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5-yl)diazene (5). Based on the single-crystal diffraction data, 5 is nearly coplanar and features face-to-face and wavelike crystal stackings, thereby exhibiting an excellent density of 1.92 g cm–3. Meanwhile, the enthalpy of 5 is as high as 962.4 kJ/mol owing to its extensive high-energy N–N, C–N, and N–O bonds. Compound 5 featuring such a characteristic demonstrates high thermal stability (T d = 256 °C), good mechanical sensitivity (IS, 18 J; FS, 220 N), and superior detonation performance (D, 9240 m s–1; P, 37.5 GPa). The combination of advanced performance and desirable security make it a potential replacement for the commonly used explosives RDX and HMX.

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“…The resonances of the nitramine moiety are found in the typical regions, with the nitro group at −45.6 ppm and the amine resonance at −184.6 ppm. 19,21 Because of the low solubility and quick decomposition even in cold methanol, only 14 As already mentioned above, 2 is bench-stable but decomposes rapidly in solution at ambient temperature, especially in protic solvents. The decomposition of 2 probably does not proceed via a Curtius rearrangement to the isocyanate, as usually occurs for carbonyl azides.…”

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confidence: 99%

“…The assignments of N β (Δν 1/2 = 50 Hz) and N γ (Δν 1/2 = 140 Hz) were based on the line widths of the resonances in the corresponding 14 N NMR spectrum. The resonances of the nitramine moiety are found in the typical regions, with the nitro group at −45.6 ppm and the amine resonance at −184.6 ppm. , Because of the low solubility and quick decomposition even in cold methanol, only 14 N NMR data for the NCA – anion are available. With ammonium salt 5 as a representative example, in addition to the ammonium signal (−367 ppm, Δν 1/2 = 6 Hz), four further resonances are detectable for the NCA – anion.…”

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confidence: 99%

Nitrocarbamoyl Azide O₂NN(H)C(O)N₃: A Stable but Highly Energetic Member of the Carbonyl Azide Family

et al. 2021

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The diazotization of nitrosemicarbazide (1) resulted in the formation and isolation of nitrocarbamoyl azide (2), which was thoroughly characterized by spectroscopic and structural methods. This compound shows surprising stability but also high reactivity and sensitivity, with a melting point of 72 °C and a detonative decomposition point at 83 °C. In addition, five selected salts were synthesized by careful deprotonation. The decomposition mechanism of 2 in solution was investigated and could be clarified by performing experiments using methanol and hydrazine as trapping reagents. The energetic and physicochemical properties of all these compounds were investigated and classified.

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Synthesis, Characterization and Properties of Ureido‐Furazan Derivatives

Cited by 21 publications

References 42 publications

Chemical Descriptors for a Large-Scale Study on Drop-Weight Impact Sensitivity of High Explosives

Chemical Descriptors for a Large-Scale Study on Drop-Weight Impact Sensitivity of High Explosives

C₈N₁₂O₈: A Promising Insensitive High-Energy-Density Material

Nitrocarbamoyl Azide O₂NN(H)C(O)N₃: A Stable but Highly Energetic Member of the Carbonyl Azide Family

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Synthesis, Characterization and Properties of Ureido‐Furazan Derivatives

Cited by 21 publications

References 42 publications

Chemical Descriptors for a Large-Scale Study on Drop-Weight Impact Sensitivity of High Explosives

Chemical Descriptors for a Large-Scale Study on Drop-Weight Impact Sensitivity of High Explosives

C8N12O8: A Promising Insensitive High-Energy-Density Material

Nitrocarbamoyl Azide O2NN(H)C(O)N3: A Stable but Highly Energetic Member of the Carbonyl Azide Family

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C₈N₁₂O₈: A Promising Insensitive High-Energy-Density Material

Nitrocarbamoyl Azide O₂NN(H)C(O)N₃: A Stable but Highly Energetic Member of the Carbonyl Azide Family