AI Article Synopsis
- The study measured binding constants of various synthetic receptor molecules to different small carboxylate anions using NMR techniques, resulting in four binding affinity scales anchored to indolocarbazole.
- Findings show that while binding strength is mainly influenced by hydrogen-bonding interactions and anion basicity, there can be deviations in binding order based on specific anions, particularly with trimethylacetate.
- Principal component analysis indicated that the unique binding patterns are likely due to added hydrophobic/solvophobic effects, which can inform better receptor design for targeting carboxylate anions.
Article Abstract
The binding constants (log Kass ) of small synthetic receptor molecules based on indolocarbazole, carbazole, indole, urea and some others, as well as their combinations were measured for small carboxylate anions of different basicity, hydrophilicity and steric demands, that is, trimethylacetate, acetate, benzoate and lactate, in 0.5 % H2 O/[D6 ]DMSO by using the relative NMR-based measurement method. As a result, four separate binding affinity scales (ladders) including thirty-eight receptors were obtained with the scales anchored to indolocarbazole. The results indicate that the binding strength is largely, but not fully, determined by the strength of the primary hydrogen-bonding interaction. The latter in turn is largely determined by the basicity of the anion. The higher is the basicity of the anion the stronger in general is the binding, leading to the approximate order of increasing binding strength, lactate
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http://dx.doi.org/10.1002/chem.201405858 DOI Listing Publication Analysis
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