Diazeniumdiolate and Sydnone Energetic Compounds Carla Holman and Navamoney Arulsamy Department of Chemistry, University of Wyoming Abstract Syntheses.

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Diazeniumdiolate and Sydnone Energetic Compounds Carla Holman and Navamoney Arulsamy Department of Chemistry, University of Wyoming Abstract Syntheses DSC Data New diazeniumdiolate & sydnone-N-oxide salts are synthesized and identified by spectral and X-ray data. Thermal (DSC) studies reveal exothermic decomposition. Compound Tonset, Tmax,˚C ΔH, cal/g ΔH, cal/mol MeN2O2K 326, 331 -340 -38800 EtN2O2K 275, 280 -245 -31400 n-PrN2O2K 266, 279 -395 -56170 i-PrN2O2K 285, 292 -235 -33420 CH(NOH)N2O2K 218, 222 -350 -50100 MeC(NOH)N2O2K 182, 183 -251 -55010 EtC(NOH)N2O2K 176, 177 -332 -56890 PhC(N2O2K)2CO2Me 196, 197 -86800 PhC2N2O3K 264, 266 -315 -68040 CH3COC2N2O3K 267, Introduction High energy density materials (HEDM) are potential jet fuels,and are of great interest to NASA.1Nitrogen-rich HEDM’s release N2 on decomposition, and are considered green fuels.2We have synthesized new energetic materials from less expensive substances. Two methods of nitrosylation: one with nitrous acid and another with NO gas at ca. 2 atm pressure are employed successfully. Both cis and trans addition of (NO)2 are observed. Conclusions The readily synthesized new HEDM’s are quite stable under ambient conditions, but exothermically decompose at high temperatures. The isolated sydnone-N-oxide salts demonstrate the trans addition of dimeric nitric oxide to nucleophiles. Structures and DSC References Nitric Oxide Reactor Klapötke, T. M. in High Energy Density Materials. Springer: Berlin, 2007, pp 85–122. Giles, J. Nature, 2004, 427, 580–581. Acknowledgement This work was funded by the Wyoming Space Grant Consortium: NASA Grant #NNG05G165H. Gerald E. Forney, Jr., and Dr. T. F. Turner, WRI, for the DSC data. Thanks. Presented at: University of Wyoming Undergraduate Research Day, April 24, 2010.