Energetic materials containing fluorine. Design, synthesis and testing of furazan-containing energetic materials bearing a pentafluorosulfanyl group

• Published in: Journal of fluorine chemistry Vol. 143; pp. 112 - 122
• Main Authors: Martinez, Henry, Zheng, Zhaoyun, Dolbier, William R.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01-11-2012
• Subjects: Basicity; Energetic materials; Furazan; Nucleophilicity; Pentafluorosulfanyl group; Pentafluorosulfanyl group; Basicity; Nucleophilicity; Furazan; Energetic materials
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2012.03.010

Ten new SF5-containing furazan materials have been synthesized and their energetic properties examined. [Display omitted]
► Pentafluorosulfanylacetic acid is a useful building block for preparation of new furazan energetic materials. ► SF5-substituted furazans have densities greater than materials containing either moiety alone. ► SF5-substituted furazans have enhanced energetic properties when compared to materials containing either moiety alone. ► The low nucleophilicity of aminofurazans makes synthesis of derivatives challenging.
The advantageous impact of a pentafluorosulfanyl substituent on the properties of furazan-containing energetic materials was demonstrated by the synthesis and study of the energetic properties of ten new compounds. The thermal stability of these compounds was evaluated by DSC and TGA, whereas densities, heats of formation, pressures of detonation and speeds of detonation were obtained computationally. On the basis of these data, it was concluded that the combination of the SF5 substituent with the furazan ring led to materials of higher density and predicted detonation properties than other known furazans or SF5-containing materials. In addition, the synthetic studies provided insight regarding the electron-withdrawing nature of the furazan ring, in particular its effect on the basicity and nucleophilic reactivity of amino furazans.