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5-(1H-Tetrazolyl)-2-Hydroxy-Tetrazole: A Selective 2N-Monoxidation of Bis(1H-Tetrazole) (CROSBI ID 228091)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Klapotke, Thomas ; Kurz, Matthias, Scharf, Regina ; Schmid, Philipp ; Stierstorfer, Jorg ; Sućeska, Muhamed 5-(1H-Tetrazolyl)-2-Hydroxy-Tetrazole: A Selective 2N-Monoxidation of Bis(1H-Tetrazole) // ChemPlusChem, 80 (2015), 1; 97-106. doi: 10.1002/cplu.201402124

Podaci o odgovornosti

Klapotke, Thomas ; Kurz, Matthias, Scharf, Regina ; Schmid, Philipp ; Stierstorfer, Jorg ; Sućeska, Muhamed

engleski

5-(1H-Tetrazolyl)-2-Hydroxy-Tetrazole: A Selective 2N-Monoxidation of Bis(1H-Tetrazole)

Sodium 5-cyanotetrazolate sesquihydrate (1) is prepared from sodium azide and two equivalents of sodium cyanide under acidic conditions. 1 is then N-oxidized with Oxone to sodium 5-cyanotetrazolate monohydrate (2). Compound 2 is treated with sodium azide and a Lewis acid to form 5-(1H-tetrazolyl)-2-hydroxytetrazole monohydrate (3). Compound 3 can be deprotonated twice by various bases to give ionic derivatives such as the bis(hydroxylammonium) (4), bis(hydrazinium) (6), bis(-guanidinium) (7), bis(aminoguanidinium) (8), bis(ammonium) (9), and diaminouronium (11) salt. In addition, compound 3 can only be deprotonated once, as demonstrated by the hydroxylammonium (4) and triaminoguanidinium (10) salts. Compounds 2–5 and 10–11 are structurally characterized by singlecrystal X-ray diffraction. Additionally, compounds 2–11 are characterized by using NMR and vibrational (IR, Raman) spectroscopy as well as mass spectrometry and elemental analysis. Their thermal behaviors are studied from differential thermal analysis measurements, and the sensitivities of the compounds toward shock, friction, and electrostatic discharge are determined. In addition, the heats of formation are calculated (atomization method, CBS-4M enthalpies), and several detonation/propulsion parameters are computed with the EXPLO5 code.

energetic materials ; heterocycles ; N-oxides ; tetrazoles ; X-ray diffraction

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Podaci o izdanju

80 (1)

2015.

97-106

objavljeno

2192-6506

10.1002/cplu.201402124

Povezanost rada

Kemija

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