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Temperature dependence measurements and structural characterization of trimethyl ammonium ionic liquids with a highly polar solvent.

We report the synthesis and characterization of a series of an ammonium ionic liquids (ILs) containing acetate, dihydrogen phosphate, and hydrogen sulfate anions with a common cation. To characterize the thermophysical properties of these newly synthesized ILs with the highly polar solvent N,N-dimethylformamide (DMF), precise measurements such as densities (ρ) and ultrasonic sound velocities (u) over the whole composition range have been performed at atmospheric pressure and over wide temperature ranges (25-50 °C). The excess molar volume (V(E)) and the deviation in isentropic compressibilities (Δκ(s)) were predicted using these temperature dependence properties as a function of the concentration of ILs. The Redlich-Kister polynomial was used to correlate the results. The ILs investigated in the present study included trimethylammonium acetate [(CH(3))(3)NH][CH(3)COO] (TMAA), trimethylammonium dihydrogen phosphate [(CH(3))(3)NH][H(2)PO(4)] (TMAP), and trimethylammonium hydrogen sulfate [(CH(3))(3)NH][HSO(4)] (TMAS). The intermolecular interactions and structural effects were analyzed on the basis of the measured and the derived properties. In addition, the hydrogen bonding between ILs and DMF has been demonstrated using semiempirical calculations with help of Hyperchem 7. A qualitative analysis of the results is discussed in terms of the ion-dipole, ion-pair interactions, and hydrogen bonding between ILs and DMF molecules and their structural factors. The influence of the anion of the protic IL, namely, acetate (CH(3)COO), dihydrogen phosphate (H(2)PO(4)), and hydrogen sulfate (HSO(4)), on the thermophysical properties is also provided.