Using a set of different techniques, which included single crystal X-ray, NMR, UV-vis, conductivity measurements, SAXS (small angle X-rays), ESI-MS(/MS) (electrospray (tandem) mass spectrometry), and theoretical calculations, an ample study of the structural organization and supramolecular interaction of the task-specific ionic liquid 1-methyl-3-carboxymethylimidazolium chloride (named MAI.Cl) was conducted. All techniques allowed for comprehensive investigation in the solid state, solution, and gas-phase behavior of MAI.Cl. Most relevant interactions are demonstrated showing the importance of hydrogen bonding to supramolecular organization of MAI.Cl in different states and its tendency to aggregate in aqueous solutions. © 2014 American Chemical Society.118311787817889Hallett, J.P., Welton, T., Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2 (2011) Chem. 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