Tautomerism and  1 H,  13 C and  15 N NMR spectral assignments of some nitro derivatives of malonic acid diamide | Zendy

Sebban Muriel | Zendy; Guillard Jérome | Zendy; Palmas Pascal | Zendy; Poullain Didier | Zendy

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Tautomerism and 1 H, 13 C and 15 N NMR spectral assignments of some nitro derivatives of malonic acid diamide

Author(s) -

Sebban Muriel,

Guillard Jérome,

Palmas Pascal,

Poullain Didier

Publication year - 2005

Publication title -

magnetic resonance in chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.483

H-Index - 72

eISSN - 1097-458X

pISSN - 0749-1581

DOI - 10.1002/mrc.1592

Subject(s) - chemistry , tautomer , malonic acid , nitration , thermal decomposition , reactivity (psychology) , nmr spectra database , carbon 13 nmr , nitro , proton nmr , nitric acid , medicinal chemistry , organic chemistry , spectral line , physics , astronomy , medicine , alternative medicine , alkyl , pathology

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 1 H, 13 C and 15 N 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 1 H and 13 C NMR spectra (ACD). Copyright © 2005 John Wiley & Sons, Ltd.

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