Repository logo
 

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

Published version
Peer-reviewed

Type

Article

Change log

Authors

Cook, Joanne L 
Hunter, Christopher A  ORCID logo  https://orcid.org/0000-0002-5182-1859

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.

Description

Keywords

Journal Title

Chemical science

Conference Name

Journal ISSN

2041-6520

Volume Title

11

Publisher

Sponsorship
Engineering and Physical Sciences Research Council (EP/K025627/2)