The acid dissociation constants of o-aminophenol and o-aminobenzenethiol and the stability constants of the chelates of these reagents with some common divalent metals have been determined by potentiometric titration techniques. The chelates of o-aminophenol are less stable than those of o-aminobenzenethiol, despite the greater acidity of the latter reagent. This is attributed to the probably greater covalent character of the metal-sulfur bond than that of metal-oxygen bond. While the order of stability of metal chelates in o-aminophenol and o-aminobenzenethiol is similar to that observed in beta-diketones and salicylaldehydes, there are some significant differences. Finally, the reactions of the o-aminophenol and o-amino-benzenethiol with metals have been observed and tabulated.
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Charles et al. (1952) studied this question.