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Hydrogen atom abstraction from hydrocarbons by a copper(III)-hydroxide complex.

Debanjan Dhar1, William B Tolman

  • 1Department of Chemistry and Center for Metals in Biocatalysis, University of Minnesota , 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.

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|January 13, 2015
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Summary

This study investigates the high reactivity of a copper complex (LCuOH) in hydrogen atom abstraction reactions. Researchers determined its thermodynamic properties and reaction kinetics, revealing insights into its potent oxidizing capabilities for catalysis.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Reaction Mechanisms

Background:

  • Copper complexes are increasingly studied for their catalytic applications.
  • Understanding the reactivity of copper-hydroxo species is crucial for designing efficient oxidation catalysts.
  • The specific complex LCuOH (1) exhibits high reactivity in hydrogen atom abstraction (HAT).

Purpose of the Study:

  • To elucidate the basis for the high rate of hydrogen atom abstraction (HAT) by the LCuOH complex.
  • To determine the bond dissociation enthalpy (BDE) of the O-H bond in the reaction product LCu(H2O) (2).
  • To investigate the oxidizing power and reaction kinetics of LCuOH with various substrates.

Main Methods:

  • Determination of pK(a) and electrochemical half-wave potential (E(1/2)) of LCu(H2O) (2) in THF.
  • Characterization of an equilibrium between LCu(H2O) (2) and LCu(THF) using UV-vis, EPR, and cyclic voltammetry (CV).
  • Kinetic studies of LCuOH (1) reactions with substrates possessing varying C-H bond BDEs in 1,2-difluorobenzene (DFB) solvent.
  • Cyclic voltammetry experiments in THF to study the reaction with THF, including kinetic isotope effect measurements.

Main Results:

  • The O-H BDE of LCu(H2O) (2) was determined to be 90 ± 3 kcal mol(-1), significantly high for transition metal oxo/hydroxo complexes.
  • LCuOH (1) demonstrated potent oxidizing power, with accelerated decay observed in the presence of substrates like THF and cyclohexane.
  • Reaction of LCuOH (1) with THF proceeded via rate-determining attack at C-H(D) bonds, exhibiting a kinetic isotope effect of 10.2.

Conclusions:

  • The high O-H bond dissociation enthalpy of the copper-aqua complex contributes to the potent oxidizing ability of LCuOH.
  • Kinetic and thermodynamic data provide insights into the high reactivity of LCuOH, supporting its potential role in oxidation catalysis.
  • The study highlights the importance of characterizing both thermodynamic stability and kinetic reactivity for understanding catalytic mechanisms.