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Chem Soc Rev. 2008 Feb;37(2):263-77. doi: 10.1039/b612543n. Epub 2007 Aug 17.

Selectivity in supramolecular host-guest complexes.

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FR Organische Chemie, Universit├Ąt des Saarlandes, D 66041 Saarbr├╝cken, Germany.


The background of possible selectivity-affinity correlations and their limitations is reviewed, with typical crown ether and cryptand complexes, ionic associations, hydrogen bonded complexes and complexes driven by van der Waals, stacking or hydrophobic interactions, with some additional topics including associations based on metal coordination as supplementary material. This tutorial review is addressed to students and researchers interested in molecular recognition, and relates to the design of sensors, of discriminators for separation processes, of supramolecular devices and of drug compounds. A theoretical analysis of selectivity in supramolecular host-guest complexes, defined as a difference in binding free energies for structurally related guests, as a function of total binding free energy shows that for certain types of intermolecular interactions one may observe a correlation between selectivity and affinity. Such correlation fails however if the selectivity is due to additional interactions at a secondary binding sites, which is expected in complexes with anisotropic guest molecules. Several clear examples of theoretically expected selectivity-affinity correlations are found. The influence of reaction conditions on the experimentally observed selectivity, defined as a difference in complexation degrees with different guests in the presence of added receptor, is illustrated. The importance of often neglected solvent effects on selectivity is exemplified with ionophore and hydrogen bonded complexes.

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