Thiol Acidities and Thiolate Ion Reactivities toward Butyl Chloride in Dimethyl Sulfoxide Solution. The Question of Curvature in Broensted Plots

Article abstract of DOI:10.1021/jo00138a005

Acidities of 15 benzenethiols and 5 aliphatic thiols have been measured in dimethyl sulfoxide solution.Homohydrogen bonding of the type PhS(1-)-HSPh, which is strong for phenols in Me2SO, is absent from thiophenols.On the other hand, evidence for strong i