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Catalytic Mechanism for the Biomimetic Oxidation of Benzoin by p-Benzoquinone in the Presence of Complexes with Bulky Arenethiolate or Cysteine-containing Tripeptide Ligands

DOI: 10.1039/DT9910000249

Source and publish data:

Journal of the Chemical Society, Dalton Transactions p. 249 - 253 (1991)

Update date:2022-08-04

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Authors:

Sugawara, TakashiSugawara, Takashi

Ueyama, NorikazuUeyama, Norikazu

Nakamura, AkiraNakamura, Akira

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Article abstract of DOI:10.1039/DT9910000249

Catalytic oxidation of benzoin to benzil by p-benzoquinone in the presence of 2 (tipbt = 2,4,6-triisopropylbenzenethiolate) obeys first-order kinetics in concentrations of benzoin and the catalyst.The observed rate constant was found to depend on the bulkiness of the thiolate or the peptide ligand of 2-.A complex with a bulky peptide, 2- ( Z = benzyloxycarbonyl, CysS = S-deprotonated cysteinate), had an activity five times higher than that of 2-. para-Substitution of benzoin indicated a trend in the oxidation rate: 4-Cl > H, 4-OMe.It is proposed that the methine hydrogen of benzoin is released as a proton in the rate-determining step.This is supported by the isotope effect (kH/kD 2.5:1) on the oxidation rate of α-C-deuteriated benzoin.An increase in the relative permittivity of the solvent results in an increase in the rate constant, indicating a polar transition state.

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