Abstract
Acidities are commonly measured in polar solvents but catalytic reactions are typically carried out in nonpolar media. IR spectra of a series of phenols in CCl4 and 1% CD3CN/CCl4 provide relative acidities. Nonprotonated charged substituents with an appropriate counterion are found to enhance their Brønsted acidities and improve catalyst performance by orders of magnitude.
Supporting Information
Experimental and computational sections including synthetic procedures, NMR spectra, and calculated structures and energies along with the complete citation to ref 18 are provided. This material is available free of charge via the Internet at http://pubs.acs.org.
