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Issue 41, 2017
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An interesting 1,4,2,5-dioxadiazine-furazan system: structural modification by incorporating versatile functionalities

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Abstract

Herein, the 1,4,2,5-dioxadiazine ring is combined with two furazan rings. Interestingly, the structure of the 1,4,2,5-dioxadiazine-furazan system can be modified by incorporating versatile functionalities. The N-trinitroethylamino functionalization derivatives and energetic salts based on 3,6-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,4,2,5-dioxadiazine are investigated. Derivatives of these functionalities are synthesized and fully characterized via multinuclear NMR spectroscopy, IR spectroscopy, and elemental analysis. The structures of compounds 1–7 are further confirmed by single-crystal X-ray diffraction. Compounds 1–12 have moderate thermal stabilities (143–177 °C, except 2 (114 °C), and 3 (88 °C)) and exhibit acceptable sensitivities (IS 3.52–16.3 J and FS 100–240 N). Based on the measured densities (1.73–1.95 g cm−3) and heats of formation (573.5–2065.4 kJ mol−1), the detonation velocities (D 8519–9563 m s−1) and pressures (P 29.3–43.3 GPa) are calculated. Among them, the trinitroethylamino derivative 1 and ammonium salt of 3,6-bis(4-nitroamino-1,2,5-oxadiazol-3-yl)-1,4,2,5-dioxadiazine 5 show a layered assembly of the 1,4,2,5-dioxadiazine-furazan system. These two compounds show good thermal stabilities (1, 154 °C and 5, 177 °C) and relatively low sensitivities (1, 16.3 J and 5, 13.4 J). These properties indicate that the layer assembly structure is helpful to improve the thermal stabilities and result in low sensitivities for the corresponding compounds.

Graphical abstract: An interesting 1,4,2,5-dioxadiazine-furazan system: structural modification by incorporating versatile functionalities

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Publication details

The article was received on 09 Jun 2017, accepted on 18 Sep 2017 and first published on 19 Sep 2017


Article type: Paper
DOI: 10.1039/C7DT02098H
Citation: Dalton Trans., 2017,46, 14301-14309
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    An interesting 1,4,2,5-dioxadiazine-furazan system: structural modification by incorporating versatile functionalities

    Q. Yu, G. Cheng, X. Ju, C. Lu, Q. Lin and H. Yang, Dalton Trans., 2017, 46, 14301
    DOI: 10.1039/C7DT02098H

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