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DFT Study of (1R,2R,4R)-Limonene-1,2-Diol Synthesized by Hydrolysis of cis and trans Limonene Oxide

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Abstract

In this study, we investigate the reaction between water and the cis and trans limonene oxide mixture in the presence of ethyl carbamate ((R)-N-(α-methyl-benzyl)ethyl-carbamate), producing (1 R, 2 R, 4 R)-limonene-1,2-diol and trans limonene oxide. This study is carried out using the quantum mechanical density functional theory (DFT) method B3LYP-D3/6-31+G (d,p) to theoretically explain that 1,2-limonene diol is the hydrolysis product derived from cis limonene oxide, with trans limonene oxide not reacting (regioselectivity). For this reason, we exploit Fukui`s frontier molecular orbital theory (FMO), local softness and local hardness ratios, transition states of the obtained products, the Fukui indices, and the thermodynamic quantities (enthalpy, entropy, free energy calculations). The theoretical results effectively elucidate the observed regioselectivity and corroborate the experimental findings.

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Authors and Affiliations

  1. Bio-Geosciences and Material Engineering Laboratory, Ecole Normale Superieure, Hassan II University, Casablanca, Morocco

    A. Nassri, M. M. El Hammoumi & A. El Bachiri

  2. Language, Literature, Imaginary, and Esthetic Laboratory, Sidi Mohamed Ben Abdellah University, Fes, Morocco

    S. El Youssfi

  3. Applied Organic Chemistry Laboratory, Faculty of Science and Technology, Sidi Mohamed Ben Abdellah University, Fes, Morocco

    M. M. El Hammoumi & Y. Kandri Rodi

  4. Engineering, Modelisation, and Systems Analysis Laboratory, Sidi Mohamed Ben Abdellah University, Fes, Morocco

    A. Touimi Benjelloun

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  1. A. Nassri
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  2. M. M. El Hammoumi
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  3. A. El Bachiri
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  4. S. El Youssfi
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  6. A. Touimi Benjelloun
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Correspondence to A. Nassri, M. M. El Hammoumi, A. El Bachiri, S. El Youssfi, Y. Kandri Rodi or A. Touimi Benjelloun.

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Text © The Author(s), 2024, published in Zhurnal Strukturnoi Khimii, 2024, Vol. 65, No. 5, 125906.https://doi.org/10.26902/JSC_id125906

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Nassri, A., El Hammoumi, M.M., El Bachiri, A. et al. DFT Study of (1R,2R,4R)-Limonene-1,2-Diol Synthesized by Hydrolysis of cis and trans Limonene Oxide. J Struct Chem 65, 859–867 (2024). https://doi.org/10.1134/S0022476624050019

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