Five new lipophilic dicarboxylic acids with systematic structural variation in the bridge which joins the two lipophilic carboxylic acid units have been synthesized. Potentiometric equilibrium measurements of hydrogen ion concentrations have been employed to determine the protonation constants for these lipophilic di-ionizable acyclic ligands in 90% methanol-10% water (v/v) at 25.0 °C and an ionic strength of 0.10 M and the stability constants for their complexes with Mg2+, Ca2+, and Sr2+. Although all five ligands exhibit the highest stability constants for Ca2+, the magnitude of the differences between the stability constants for complexation of Ca2+ versus Mg2+ or Sr2+ is found to vary widely depending upon the identity of the bridging unit which joins the two carboxylic acid end groups.
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Cho, M.H., Yu, S.H., Utterback, M.D. et al. Thermodynamic studies of alkaline-earth-metal cation complexation by lipophilic dioxa, trioxa, and dithia dicarboxylic acids. J Incl Phenom Macrocycl Chem 20, 131–142 (1994). https://doi.org/10.1007/BF00709337
- Stability constants
- protonation constants
- di-ionizable lipophilic podands