Boronic Acid Catalyzed Hydrolyses of Salicylaldehyde Imines

Article abstract of DOI:10.1021/jo00004a031

The hydrolysis of salicylaldehyde imines is catalyzed by boric acid, substituted arylboronic acids, and diphenylboronic acid.These reactions show saturation kinetics, allowing the determination of first-order catalytic constants and dissociation constants.Dissociation constants reflect single-ionization pK values similar to the pK values of the boronic acids.Binding is best on the acid side of the pK.Use of the Bronsted and the Hammett Catalytic constants are nearly independent of pH, of Hammett ?, and of the pK of the catalyst.The reactions display no solvent deuterium isotope effect.