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New Kemp’s Diacid Derivatives Give Efficient Transport and Modifiable Selectivity for Alkaline Earth and Transition Metal Ions

New derivatives of 1,3,5-trimethyl-r-1, c-3, c-5-cyclohexanetricarboxylic acid (Kemp’s triacid) showed high efficiency for alkaline earth and transition metal ion transport through a chloroform liquid membrane. Simple syntheses from Kemp’s triacid or its geometric isomer provided chelating agents with a tripodal binding site for metal cations. The tripodal binding site consisted of r-1, c-3-diaxial carboxyl group and a c-5-amide, ester, or C-methyl group. Alkaline earth metal transport was quite variable and sensitive to c-5-group changes. For transition metal transport, c-5-amide diacids gave high total transport efficiency. For c-5-ester or C-methyl diacids, complexation of smaller divalent cations was decreased, resulting in increased selectivity for large cations.