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Selective Oxidation of L-Methionine, L-Ethionine, N-Acetyl-L-Methionine, L-Buthionine Catalyzed by [FeIII-Salen]Cl Complexes: A Spectral, Kinetic, and Electrochemical Study

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Abstract

This present study aims to report the spectral, kinetic, and electrochemical results of the selective oxidation of substrates such as L-methionine (I), L-ethinonine (II), L-buthionine (III), and N-acetyl-L-methionine (IV) with [O=FeIV-salen]\(^{{ \bullet + }}\) oxidant species 1a–5a in aqueous CH3CN under biological conditions. Reactions between oxidants and the substrates follow saturation kinetics (Michalis-Menton type), and this reaction is very sensitive with the substituents present in salen ligand of the complex, structure of substrates I–IV, the effects of pH, substrate concentration, the polarity of the solvent, and temperature. The [O=FeIV-salen]\(^{{ \bullet + }}\) oxidant species is confirmed by spectral and electrochemical techniques. The positive reaction constants (ρ = 0.79–0.90) are obtained from the plot of rate constant (k) values versus substituent constants (σ) values, which indicates the development of negative charge in the transition state (TS). The formation of the product during the course of reaction is analyzed by FT-IR, ESI-MS, and 1H-NMR techniques. Based on the experimental evidences a plausible electron transfer (ET) and oxygen atom transfer (OAT) mechanisms have been proposed.

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ACKNOWLEDGMENTS

The author thanks the PG and Research Department of Chemistry, Vivekananda College, Tiruvedakam West, Madurai-625 234 for providing research facilities.

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  1. Post Graduate and Research Department of Chemistry, Vivekananda College, 625234, Tiruvedakam, Madurai District, Tamil Nadu, India

    Periyakaruppan Karuppasamy

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Karuppasamy, P. Selective Oxidation of L-Methionine, L-Ethionine, N-Acetyl-L-Methionine, L-Buthionine Catalyzed by [FeIII-Salen]Cl Complexes: A Spectral, Kinetic, and Electrochemical Study. Russ. J. Phys. Chem. 95 (Suppl 2), S230–S241 (2021). https://doi.org/10.1134/S0036024421150127

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