Azolium salts functionalized with cyanomethyl, vinyl, or propargyl substituents and dicyanamide, dinitramide, perchlorate and nitrate anions

A series of functionalized imidazoliurn and 1,2,4-triazolium salts with cyanomethyl, vinyl and propargyl substituents coupled with energetic anions, viz., perchlorate, nitrate, dicyanamide and dinitramide were prepared and characterized by NMR and IR spectroscopy, and elemental analyses. Since some melt < 100 degrees C, they can be classed as ionic liquids. Their densities range between 1.25-1.76 g cm(-3). The standard enthalpies of formation of the salts were calculated by using the computationally feasible DFT(B3LYP) and MP2 methods in conjunction with an empirical approach based on calculated densities of the salts. These values range from Delta H degrees(f) = -56 (12a) to 851 (21c) kJmol(-1). Of the salts synthesized, the dicyanamides exhibit the highest positive heats of formation, but also the lowest densities. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).