Tautomerism and 1H, 13C and 15N NMR spectral assignments of some nitro derivatives of malonic acid diamide |
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Authors: | Sebban Muriel Guillard Jérome Palmas Pascal Poullain Didier |
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Institution: | Commissariat à l'Energie Atomique, BP 16, 37260 Monts, France. |
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Abstract: | Because of its reactivity, malonic acid diamide (1) was initially identified as an alternative precursor for the development of a new class of high-density insensitive energetic materials possessing low sensitivity to thermal decomposition and detonation by impact. Nitration of 1 was studied under different conditions and led to three different tautomeric forms (2-4) of nitromalonic acid diamine. Using stronger oxidation conditions the oxadiazole 5 was generated in one step. We report the full 1H, 13C and 15N NMR structural characterization of these compounds in DMSO together with thermal, infrared, mass spectrometric and x-ray analysis. Experimental data obtained for 4 are compatible with an enol-imine form. Our interpretation is consistent with calculated 1H and 13C NMR spectra (ACD). |
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