Functional group interaction profiles: a general treatment of solvent effects on non-covalent interactions.

Chemical Science
Mark D DriverChristopher A Hunter

Abstract

Solvation has profound effects on the behaviour of supramolecular systems, but the effects can be difficult to predict even at a qualitative level. Functional group interaction profiles (FGIPs) provide a simple visual method for understanding how solvent affects the free energy contribution due to a single point interaction, such as a hydrogen bond, between two solute functional groups. A generalised theoretical approach has been developed, which allows calculation of FGIPs for any solvent or solvent mixture, and FGIPs for 300 different solvents have been produced, providing a comprehensive description of solvent effects on non-covalent chemistry. The free energy calculations have been validated using experimental measurements of association constants for hydrogen bonded complexes in multiple solvent mixtures. The calculated FGIPs provide good descriptions of the solvation of polar solutes, solvophobic interactions between non-polar solutes in polar solvents like water, and preferential solvation in solvent mixtures. Applications are explored of the use of FGIPs in drug design, for optimising receptor-ligand interactions, and in enantioselective catalysis for solvent selection to optimise selectivity.

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Citations

Jun 15, 2021·Chemical Science·Christopher D JonesJonathan W Steed
May 16, 2020·Physical Chemistry Chemical Physics : PCCP·Mark D Driver, Christopher A Hunter
Sep 15, 2020·Chemistry : a European Journal·Stephanie A BoerNicholas G White
Jan 23, 2021·Physical Chemistry Chemical Physics : PCCP·Nikola StamenkovićJanez Cerkovnik
Feb 18, 2021·Journal of the American Chemical Society·Yun LiuAmar H Flood
Apr 14, 2021·The Journal of Physical Chemistry. B·Ennio LavagniniChristopher A Hunter
Nov 12, 2020·Journal of the American Chemical Society·Mathijs F J MabesooneE W Meijer
Oct 12, 2021·Physical Chemistry Chemical Physics : PCCP·Reyes Núñez-FrancoAntonio Franconetti
Oct 30, 2021·Journal of Chemical Information and Modeling·Mark D DriverChristopher A Hunter

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Methods Mentioned

BETA
footprinting
interaction profiles

Software Mentioned

SSIMPLE

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