The Use of Hammett Constants to Understand the Non-covalent Binding of Aromatics
Overview
Affiliations
Non-covalent interactions of aromatics are important in a wide range of chemical and biological applications. The past two decades have seen numerous reports of arene-arene binding being understood in terms Hammett substituent constants, and similar analyses have recently been extended to cation-arene and anion-arene binding. It is not immediately clear why electrostatic Hammett parameters should work so well in predicting the binding for all three interactions, given that different intermolecular forces dominate each interaction. This review explores such anomalies, and summarizes how Hammett substituent constants have been employed to understand the non-covalent binding in arene-arene, cation-arene and anion-arene interactions.
Sigma Hole Potentials as Tools: Quantifying and Partitioning Substituent Effects.
Donald K, Pham N, Ravichandran P J Phys Chem A. 2023; 127(48):10147-10158.
PMID: 38058158 PMC: 10711721. DOI: 10.1021/acs.jpca.3c05797.
Effect of a Substituent on the Properties of Salicylaldehyde Hydrazone Derivatives.
Hoelm M, Adamczyk J, Wzgarda-Raj K, Palusiak M J Org Chem. 2023; 88(4):2132-2139.
PMID: 36735741 PMC: 9942203. DOI: 10.1021/acs.joc.2c02547.
Sacristan-Martin A, Miguel D, Diez-Varga A, Barbero H, Alvarez C J Org Chem. 2022; 87(24):16691-16706.
PMID: 36454642 PMC: 9764357. DOI: 10.1021/acs.joc.2c02345.
Elucidating the Mechanism of Excited-State Bond Homolysis in Nickel-Bipyridine Photoredox Catalysts.
Cagan D, Bim D, Silva B, Kazmierczak N, McNicholas B, Hadt R J Am Chem Soc. 2022; 144(14):6516-6531.
PMID: 35353530 PMC: 9979631. DOI: 10.1021/jacs.2c01356.
Dissection of the Polar and Non-Polar Contributions to Aromatic Stacking Interactions in Solution.
Bravin C, Piekos J, Licini G, Hunter C, Zonta C Angew Chem Int Ed Engl. 2021; 60(44):23871-23877.
PMID: 34472177 PMC: 8596670. DOI: 10.1002/anie.202110809.