Density Functional Theory Studies on the Mechanism of the Reduction of CO2 to CO Catalyzed by Copper(l) Boryl Complexes.

The detailed reaction mechanism for the reduction of CO to CO catalyzed by (NHC)Cu(boryl) complexes (NHC = N-heterocyclic carbene) was studied with the aid of DFT by calculating the relevant intermediates and transition state structures. Our DFT calculations show that the reaction occurs through CO...

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Publicado en:Journal of the American Chemical Society Vol. 128; no. 49; pp. 15637 - 15644
Autores principales: Haitao Zhao, Zhenyang Lin, Marder, Todd B.
Formato: Artículo
Publicado: American Chemical Society 12/13/2006
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Acceso en línea:Ver este registro en EBSCOhost
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      dt: 12/13/2006
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        10.1021/ja063671r
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        atl: Density Functional Theory Studies on the Mechanism of the Reduction of CO2 to CO Catalyzed by Copper(l) Boryl Complexes.
      aug:
        au:
          Haitao Zhao
          Zhenyang Lin
          Marder, Todd B.
        affil:
          Department of Chemistry and Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong
          Department of Chemistry, Durham University, South Road, Durham DHJ 3LE, U.K.
      su:
        Density functionals
        Reaction mechanisms (Chemistry)
        Copper compounds
        Functional analysis
        Conditions & laws of chemical reaction
        Physical & theoretical chemistry
      sug:
        subj:
          Density functionals
          Reaction mechanisms (Chemistry)
          Copper compounds
          Functional analysis
          Conditions & laws of chemical reaction
          Physical & theoretical chemistry
      ab: The detailed reaction mechanism for the reduction of CO to CO catalyzed by (NHC)Cu(boryl) complexes (NHC = N-heterocyclic carbene) was studied with the aid of DFT by calculating the relevant intermediates and transition state structures. Our DFT calculations show that the reaction occurs through CO insertion into the CuB bond to give a CuOC(O)-boryl species (i.e., containing CuO and CB bonds), and subsequent boryl migration from C to O, followed by o-bond metathesis between pinB-Bpin (Bpin, pin = pinacolate = OCMeCMeO) and (NHC)Cu(OBpin). The overall reaction is exergonic by 38.0 kcal/mol. It is the nucleophilicity of the CuB bond, a function of the very strong σ-donor properties of the boryl ligand, rather than the oxophilicity of boron, which determines the direction of the CO insertion process. The boryl migration from C to O, which releases the product CO, is the rate-determining step and involves the ‘vacant’ orbital orbital on boron. The (NHC)Cu(boryl) complexes show unique activity in the catalytic process. For the analogous (NHC)Cu(alkyl) complexes, the CO insertion into the CuC bond giving a copper acetate intermediate occurs with a readily achievable barrier. However, the elimination of CO from the acetate intermediate through a methyl migration from C to O is energetically inaccessible.
      pubtype: Academic Journal
      doctype: Article
      src: R
    language: English
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