LAUSR

Abstract Electrochemical properties of a series of chiral Ni(II) Schiff-base complexes of β-arylsulfanyl amino acids were investigated; the potential values and possible follow-up steps were compared for the diastereomeric couples. Within the series, two diastereomeric couples ((D)- and (L)-1H as well as (D)- and (L)-2H) were identified which constitute an interesting example of the stereodependent reactivity induced by electrochemical oxidation: follow-up transformations of the radical-cations are different for the (L)- and (D)-diastereomers. Reversibility of electrochemical reduction of the complexes allows comparison of the reduction potential values for the diastereomeric couples. DFT computation of the conformations of (D)- and (L)- diastereomers as well as non-covalent interactions in the Ni coordination environment indicates that small differences observed in the reduction potential values are more likely attributed to solvation rather than stereoelectronic effects induced by inversion of the α-amino acid stereocenter.