Tautomerism and 1H, 13C and 15N NMR spectral assignments of some nitro derivatives of malonic acid diamide.
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).
Sebban
Muriel
M
Commissariat à l'Energie Atomique, BP 16, 37260 Monts, France.
Guillard
Jérome
J
Palmas
Pascal
P
Poullain
Didier
D
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
D002247:Carbon Isotopes; D008314:Malonates; D017672:Nitrogen Compounds; D011522:Protons; D003958:Diamide; C030290:malonic acid