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Theoretical study of the substituent effect on the O–H insertion reaction of copper carbenoids

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Abstract

In this paper, we will study the reactivity along with substituent changes in the OH insertion reaction in copper carbenoids. To this end, we have used M06-2X functional with cc-pVDZ for light atoms and LanL2DZ for copper. We have studied the IRC insertion profiles and analysed reactivity indexes such as electrophilicity (ω) and pKa calculations. We have found that with R1 substitutions phenyl group, R2 substitutions amide group lower the reaction barrier considerably. Concerning the substrate reactions, the most favoured substituent is NO2 in para position.

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Funding

This article was funded by ANID FONDECYT REGULAR No. 1170837.

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Authors and Affiliations

  1. QTC, Departamento de Química Física, Escuela de Química, Facultad de Química y de Farmacia, Pontificia Universidad Católica de Chile, Av. Vicuña Mackenna 4860, Macul, 7820436, Santiago, Chile

    Rocío Durán & Barbara Herrera

  2. Centro de Bioinformática, Simulación y Modelado (CBSM), Facultad de Ingeniería, Universidad de Talca, 1141, Talca, Chile

    Rocío Durán

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  1. Rocío Durán
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Durán, R., Herrera, B. Theoretical study of the substituent effect on the O–H insertion reaction of copper carbenoids. Theor Chem Acc 141, 15 (2022). https://doi.org/10.1007/s00214-022-02876-8

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