Energetic propane-1,3-diaminium and butane-1,4-diaminium salts of <i>N</i>,<i>N</i>′-dinitroethylenediazanide: syntheses, crystal structures and thermal properties

Roodt, Gerhard T.; Uprety, Bhawna; Levendis, Demetrius C.; Arderne, Charmaine

doi:10.1107/s2053229618017588

Cited by 2 publications

(2 citation statements)

References 30 publications

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“…]octane-3,7-dione (glycoluril), which structurally contain one or two imidazole rings, respectively. The nitration reactions of these structural precursors of THAP with mixed nitric/sulfuric acids, nitric acid, acetyl nitrate, or mixed ammonium nitrate/trifluoroacetic anhydride in nitromethane and with nitronium trifluoromethanesulfonate in dichloromethane are well-studied [ 6 , 7 , 8 , 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Nitro- and Acetyl Derivatives of 3,7,10-Trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane

et al. 2022

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Here, we report the study results of the nitration of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane (THAP) by different nitrating agents such as nitric acid, mixed nitric/sulfuric acids, nitric anhydride, and mixed concentrated nitric acid/acetic anhydride to furnish 3,7,10-trioxo-2-nitro-2,4,6,8,9,11-hexaaza[3.3.3]propellane and 3,7,10-trioxo-2,8-dinitro-2,4,6,8,9,11-hexaaza[3.3.3]propellane, whereas a lactam–lactim rearrangement was found to take place upon vigorous cooling to give 10-hydroxy-2,4,6,8,9,11-hexaazatricyclo[3.3.3.01,5]undec-9-ene-3,7-dione. The two competing reactions, lactam–lactim rearrangement, and nitration were found to take place. The acylation of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane was examined and the formation conditions of 2,6-di- and 2,6,9-triacetyl-substituted and 3,7,10-trioxo-2,4,6,8,9,11-hexaacetyl-2,4,6,8,9,11-hexaaza[3.3.3]propellane were established. The acetyl derivatives were found to be instable in an acidic medium and to undergo deacylation. The obtained findings correlate well with the quantum-chemical calculations.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Nitro- and Acetyl Derivatives of 3,7,10-Trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane

et al. 2022

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“…However, a procedure for the preparation of the lead and copper(II) salts and their utilization in explosive compositions can also be found in the literature . Besides the neutral compound, the sodium and hydrazinium as well as the corresponding 1,3-diaminopropane and 1,4-diaminobutane salts were examined crystallographically. − Only the last two structures where determined at low-temperature conditions. In addition, vibrational spectra and quantum chemical calculations predicting the structure of several salts can be found …”

Section: Introductionmentioning

confidence: 99%

Investigation of Ethylenedinitramine as a Versatile Building Block in Energetic Salts, Cocrystals, and Coordination Compounds

et al. 2021

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Ethylenedinitramine (H 2 EDN, 1) was prepared in a simple manner and with a high overall yield by direct nitration of 2imidazolidinone using 100% HNO 3 at 0 °C and subsequent hydrolysis in water at 100 °C. The versatility of 1 allows its application as starting material for a broad range of different materials. It was used for the preparation of both various salts and cocrystalline materials incorporating varying amounts of the TATOT moiety. Furthermore, H 2 EDN was successfully applied in the concept of energetic coordination compounds (ECCs) resulting in five copper(II) and two silver(I) complexes. A reaction path for the direct precipitation or slow crystallization of 17 different salts, including several alkali, alkaline earth, silver, and nitrogenrich samples, is presented. The substances were extensively characterized by low-temperature single-crystal X-ray diffraction, elemental analysis (EA), IR spectroscopy, differential thermal analysis (DTA), and thermogravimetric analysis (TGA), proving their high thermal stability, especially of the alkali salts. In addition, 1 and all salts were characterized by 1 H, 13 C, and 14 N NMR, whereas 1 was also investigated using the beneficial 1 H− 15 N HMBC NMR spectroscopy. The sensitivities toward various mechanical stimuli according to BAM standard methods, as well as ball drop impact and electrostatic discharge (ESD) were determined using the BAM 1-out-6 method. Hot plate and hot needle tests were performed, followed by further characterization of the copper(II)-based ECCs through laser ignition experiments and UV−vis spectroscopy, offering new candidates for nontoxic, less sensitive laser-ignitable materials. Several detonation parameters were calculated using EXPLO5 (V6.05.02).

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Energetic propane-1,3-diaminium and butane-1,4-diaminium salts of N,N′-dinitroethylenediazanide: syntheses, crystal structures and thermal properties

Cited by 2 publications

References 30 publications

Synthesis of Nitro- and Acetyl Derivatives of 3,7,10-Trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane

Synthesis of Nitro- and Acetyl Derivatives of 3,7,10-Trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane

Investigation of Ethylenedinitramine as a Versatile Building Block in Energetic Salts, Cocrystals, and Coordination Compounds

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