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Issue 32, 2017
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Aminoacetonitrile as precursor for nitrogen rich stable and insensitive asymmetric N-methylene-C linked tetrazole-based energetic compounds

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Abstract

Reaction of aminoacetonitrile with cyanogen azide resulted in acetonitrile derivative of amino(tetrazole), 1, which on further reaction with sodium azide in the presence of ammonium chloride resulted in compound 2 with N-methylene-C bridged tetrazole and amino-tetrazole moieties. Reaction of 2 with 100% nitric acid resulted in N-(1-((1H-tetrazol-5-yl)methyl)-1H-tetrazol-5(4H)-ylidene)nitramide (4) having N-methylene-C bridged nitroimino-tetrazole and tetrazole moieties. Various energetic salts based on these three types of tetrazole derivatives (tetrazole, amino-tetrazole and nitroimino-tetrazole) in 2 and 4 were obtained. All the compounds were thoroughly characterized by IR, NMR [1H, 13C{1H}, 15N], elemental analysis, and differential scanning calorimetry (DSC). Some of them were also structurally characterized with single-crystal X-ray diffraction studies. Heats of formation and detonation performances for all the energetic compounds were calculated using Gaussian 03 and EXPLO5 v6.01 programs, respectively.

Graphical abstract: Aminoacetonitrile as precursor for nitrogen rich stable and insensitive asymmetric N-methylene-C linked tetrazole-based energetic compounds

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Publication details

The article was received on 20 Jun 2017, accepted on 21 Jul 2017 and first published on 21 Jul 2017


Article type: Paper
DOI: 10.1039/C7TA05394K
Citation: J. Mater. Chem. A, 2017,5, 16767-16775
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    Aminoacetonitrile as precursor for nitrogen rich stable and insensitive asymmetric N-methylene-C linked tetrazole-based energetic compounds

    D. Kumar, G. H. Imler, D. A. Parrish and J. M. Shreeve, J. Mater. Chem. A, 2017, 5, 16767
    DOI: 10.1039/C7TA05394K

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