Synthesen auf dem Gebiet der Nitramine III. N-Chlormethylnitramine

Majer, J.; Denkstein, J.

doi:10.1135/cccc19662547

Cited by 16 publications

(7 citation statements)

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“…Purifications were performed by distillation or sublimation. Although NAP‐Cl was discovered 50 years ago,10a it was crystallized for the first time at –30 °C, and its X‐ray structure is compared to the previously reported gas‐phase structure;12 NAP‐NCO9 was also isolated by distillation and crystallized for the first time at –80 °C.…”

Section: Resultsmentioning

confidence: 98%

Asymmetric Carbamate Derivatives Containing Secondary Nitramine, 2,2,2‐Trinitroethyl, and 2‐Fluoro‐2,2‐dinitroethyl Moieties

et al. 2013

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In this work, the syntheses of 2,2,2‐trinitroethyl‐(2‐nitro‐2‐azapropyl)carbamate (5), its analogue 2‐fluoro‐2,2‐dinitroethyl(2‐nitro‐2‐azapropyl)carbamate (6), and the corresponding 2,2,2‐trinitroethyl(2‐nitro‐2‐azapropyl)nitrocarbamate (7) and 2‐fluoro‐2,2‐dinitroethyl(2‐nitro‐2‐azapropyl)nitrocarbamate (8) are presented. The compounds were characterized thoroughly by vibrational spectroscopy (IR and Raman), multinuclear NMR spectroscopy, mass spectrometry, elemental analysis, differential scanning calorimetry measurements and single‐crystal X‐ray diffraction. In addition, the hitherto unknown low‐temperature crystal structures of the starting materials 2‐nitro‐2‐azapropyl chloride (1) and 2‐nitro‐2‐azapropyl isocyanate (2) are presented. Owing to the positive oxygen balance of the carbamate derivatives, their suitability as potential oxidizers in energetic formulations with aluminium as the fuel is investigated and discussed. Standard enthalpies of formation were calculated at the CBS‐4M level of theory. With these values and the experimental densities from room‐temperature pycnometer measurements, several detonation parameters, such as the detonation pressures and velocities of the crude materials as well as the specific impulses of their formulations with aluminium, were computed by using the EXPLO5 (V6.01) computer program and compared with those of the corresponding mixtures with ammonium perchlorate as the oxidizer. Furthermore, the sensitivities towards impact, friction and electrostatic discharge were determined by using the BAM drop‐hammer and friction tester as well as a small‐scale electrical discharge device.

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Section: Resultsmentioning

confidence: 98%

Asymmetric Carbamate Derivatives Containing Secondary Nitramine, 2,2,2‐Trinitroethyl, and 2‐Fluoro‐2,2‐dinitroethyl Moieties

et al. 2013

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“…The reaction of salt 1 with 2 chloromethyl 5 nitro tetrazole in DMF at 75°C proceeded in a peculiar manner and afforded bis(4 nitrimido 1,2,4 triazolio 1)methane (8) in 16% yield and sodium nitrotetrazolide in 44% yield (Scheme 4) instead of the expected alkyla tion product. The salt was identified in the form of 2 acetonyl 5 nitrotetrazole.…”

Section: Methodsmentioning

confidence: 97%

“…The starting 1,2,4 triazole 4 nitrimide sodium salt mono hydrate, 7 1 chloro 2 nitro 2 azapropane, 8 1 chloro 2,4,6 trinitro 2,4,6 triazaheptane, 8 1 chloro 2,5,7 trinitro 2,5,7 triazaoctane, 8 1 chloro 4 cyano 2 nitro 2 azabutane, 9 1,3 dichloro 2 nitro 2 azapropane, 8 1,4 dichloro 2 nitro 2 azabutane, 9 1,5 dichloro 2,4 dinitro 2,4 diazapentane, 8 1,6 dichloro 2,5 dinitro 2,5 diazahexane, 10 1,7 dichloro 2,4,6 trinitro 2,4,6 triazaheptane, 8 1 tosyloxymethyl 1,2,4 triazole, 11 1 chloromethyl 5 methyltetrazole, 11 2 chloromethyl 5 nitro tetrazole, 11 and 3,4 bis(bromomethyl)furoxan 12 were obtained by the known methods. DMF and acetonitrile were dried and distilled over P 2 O 5 , diethyl ether was dried with КОН and distilled over Na wire.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 1,2,4-triazolium 4-nitrimides with polyfunctionalized substituents

2009

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“…Ammonium 5‐(fluorodinitromethyl)‐tetrazolate ( 3 ),18 potassium dinitroacetonitrile ( 4 )16, 26–28 and 2‐nitro‐azapropyl chloride ( 8 )29a were synthesised according to the literature‐known procedures and purified by re‐crystallisation (compounds 3 and 4 ) and distillation (compound 8 ).…”

Section: Methodsmentioning

confidence: 99%

New Energetic Polynitrotetrazoles

Kettner

Klapötke

2015

Chemistry A European J

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This combined experimental, theoretical and comparative study details the syntheses and chemical characterisation of two new energetic polynitromethyl tetrazole derivatives, namely, 2-(2-nitro-2-azapropyl)-5-(trinitromethyl)-2 H-tetrazole and its fluorine-containing analogue 2-(2-nitro-2-azapropyl)-5-(fluorodinitromethyl)-2 H-tetrazole. Their crystal structures and energetic behaviour are compared to those of their starting materials, the ammonium salts of the corresponding 5-(polynitromethyl)-2 H-tetrazoles. Additionally, the crystal structures of two further related polynitrotetrazoles are presented.

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Synthesen auf dem Gebiet der Nitramine III. N-Chlormethylnitramine

Cited by 16 publications

References 0 publications

Asymmetric Carbamate Derivatives Containing Secondary Nitramine, 2,2,2‐Trinitroethyl, and 2‐Fluoro‐2,2‐dinitroethyl Moieties

Asymmetric Carbamate Derivatives Containing Secondary Nitramine, 2,2,2‐Trinitroethyl, and 2‐Fluoro‐2,2‐dinitroethyl Moieties

Synthesis of 1,2,4-triazolium 4-nitrimides with polyfunctionalized substituents

New Energetic Polynitrotetrazoles

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