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Azolium Salts Functionalized with Cyanomethyl, Vinyl, or Propargyl Substituents and Dicyanamide, Dinitramide, Perchlorate and Nitrate Anions
Author(s) -
Gao Ye,
Gao Haixiang,
Piekarski Crystal,
Shreeve Jean'ne M.
Publication year - 2007
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200700666
Subject(s) - dicyanamide , chemistry , ionic liquid , perchlorate , propargyl , inorganic chemistry , standard enthalpy of formation , nitrate , medicinal chemistry , organic chemistry , catalysis , ion
A series of functionalized imidazolium 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 °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 Δ H ° f = –56 ( 12a ) to 851 ( 21c ) kJ mol –1 . Of the salts synthesized, the dicyanamides exhibit the highest positive heats of formation, but also the lowest densities. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)