The Conjugative Effects of Thia, Sulfinyl and Sulfonyl Groups on the Dissociation of p-Substituted Phenols

Abstract

Several di- or tetramethyl substituted derivatives of bis-(4-hydroxyphenyl)sulfides, sulfoxides and sulfones were newly prepared and their acid dissociations, UV and IR spectra were reinvestigated. Essentially no steric inhibition was observed in the 3-d orbital resonance with the sulfinyl and the sulfonyl groups in both the acid dissociations and the UV spectra of the substituted phenols. However, a small but noticeable steric inhibition by ortho methyl groups was observed with the mercaptophenol.