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Issue 17, 2020

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

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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.

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

Supplementary files

Article information


Submitted
02 Mar 2020
Accepted
10 Apr 2020
First published
21 Apr 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 4456-4466
Article type
Edge Article

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

M. D. Driver, M. J. Williamson, Joanne L. Cook and C. A. Hunter, Chem. Sci., 2020, 11, 4456 DOI: 10.1039/D0SC01288B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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