In this paper, physicochemical characterization of newly synthesized choline based ionic liquids with five different chelating anions were examined. The ionic liquids (ILs): cholinium-L-lactate, [Ch][Lac], cholinium-picolinate, [Ch][Pic], cholinium-anthranilate, [Ch][Ant], cholinium-oxyquinolinate, [Ch][oQ], and cholinium-diethylenetriaminepentaacetate, [Ch](3)[DTPA], were prepared for the first time and their structures were confirmed by IR and H-1 and C-13 NMR spectra. Also, thermogravimetric analysis (TGA) was applied to determine their thermal stabilities. Based on the measured density values and viscosity in the temperature range from (293.15 to 323.15) K and calculated values of thermal expansion coefficients and activation energy of viscous flow, as well as of computational simulations, the interactions and structures of the investigated ionic liquids were discussed. (C) 2018 Elsevier Ltd.