Yuval Halpern

Arylmercury compounds : VI. A proposed mechanism for the symmetrization of arylmercuric salts in the presence of chelating agents

Abstract A mechanism is proposed for the symmetrization of arylmercuric salts in the presence of chelating agents. The roles of the chelating agent and auxiliary ligand (which is necessary in most cases) are considered. The proposed mechanism includes three main steps: ( i ) dissociation of the arylmercuric salt; ( ii ) formation of a reactive complex between the ionized arylmercuric salt and the chelating agent; ( iii ) an electrophilic substitution at a CHg bond via a two-electron, three-center bond type transition state.

Arylmercury compounds : IV. Symmetrization in the absence of auxiliary ligand☆

Abstract Phenylmercuric acetate is converted into diphenylmercury via a symmetrization process, in the absence of an auxiliary ligand, when the reaction is carried out at 6.5 ≥ pH > 4.0. Arylmercuric salts, in which the aromatic rings contain more than one electron donating group, symmetrize in the absence of an auxiliary ligand when the reaction is carried out at a basic pH. Both processes can be carried out in water or in mixtures of organic solvents and water. The factors influencing the symmetrization at different pH values are discussed.