title: Tautomerism and 1H, 13C and 15N NMR spectral assignments of some nitro derivatives of malonic acid diamide.
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).
authors.affiliation: Commissariat à l'Energie Atomique, BP 16, 37260 Monts, France.
authors.forename: Muriel
authors.initials: M
authors.lastname: Sebban
authors.forename: Jérome
authors.initials: J
authors.lastname: Guillard
authors.forename: Pascal
authors.initials: P
authors.lastname: Palmas
authors.forename: Didier
authors.initials: D
authors.lastname: Poullain
mesh_terms: D002247:Carbon Isotopes; D003958:Diamide / Q000032:analysis / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008314:Malonates / Q000032:analysis / Q000737:chemistry*; D017672:Nitrogen Compounds / Q000032:analysis / Q000737:chemistry*; D011522:Protons
chemical_list: D002247:Carbon Isotopes; D008314:Malonates; D017672:Nitrogen Compounds; D011522:Protons; D003958:Diamide; C030290:malonic acid