Solvents, acceptor properties miscibility with water

A substance is readily miscible with water only if it can act as a proton acceptor in a hydrogen bond, as, for example, ketones, nitriles, ethers, alcohols and amines. Such substances are also freely miscible with inert non-polar solvents such as benzene or carbon tetrachloride. The interpretation of the properties of the latter solutions is well established and there would appear to be an analogy between them and aqueous solutions. Thus,... 

PILs containing alkylammonium cations have been investigated for their potential use in chromatography, such as eAN, ° ethylammonium acetate (EAA), ° pro-pylammonium nitrate (PAN), ° tributylammonium nitrate (TB AN), ° alkylammonium formates, and various alkylammonium thiocyanates. The early use of PILs in chromatography was primarily to characterize the solvent properties of the PILs, which was described in a comprehensive review by Poole in 2004. The solvent properties of PILs that make them potentially useful in chromatography are that they are polar, are cheap, are easy to make, can be miscible with water, can be air/moisture stable, and have high selectivity toward solutes that are polar and/or hydrogen donors or acceptors. 

---