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Structural analysis of (R)-3-methylcyclohexanone conformers

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Abstract

The electronic circular dichroism (CD) spectra as a function of temperature for R-( +)-3-methylcyclohexanone (R3MCH) were reported in 11 solvents of wide polarity range for the optically active n → π* transition band. An asymptotic approach on temperature-dependent CD data was utilized to determine conformer’s CD signal and population, in addition to determining enthalpy, entropy, and Gibbs free energy differences between the equatorial and axial conformers. The evaluated thermodynamic constants were compared with values reported in literature and found to be insensitive to solvent polarity. By comparing CD spectra in vapor and solution phases, solvent effects on CD spectra were also investigated and observed to correlate with solvent polarity and nature. Also, DFT calculations of the R3MCH dipole moment components and magnitude for the individual equatorial (EQ) and axial (AX) conformers were performed by employing a hybrid set of type B3LYP with basis set aug-cc-pVTZ and within the framework of the polarizable continuum model. The calculated dipole moment magnitudes of the dominant conformers in different solvents were observed to linearly correlate with solvent polarity.

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The author confirms that the data supporting the findings of this study are available within the article.

Code availability

All computations were performed with Gaussian 09 program. Gaussian 09 program can be obtained under academic or commercial license from Gaussian, Inc. (https://gaussian.com/).

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Funding

The support was provided by the Deanship of Scientific Research at King Fahd University of Petroleum and Minerals under Research Grant (#DF191010).

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Authors and Affiliations

  1. Department of Physics, King Fahd University of Petroleum & Minerals, Dhahran, 31261, Saudi Arabia

    Watheq Al-Basheer

  2. Interdisciplinary Research Center of Membranes and Water Security, King Fahd University of Petroleum & Minerals, Dhahran, 31261, Saudi Arabia

    Watheq Al-Basheer

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  1. Watheq Al-Basheer
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W. Al-Basheer was responsible for the overall investigations.

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Correspondence to Watheq Al-Basheer.

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Al-Basheer, W. Structural analysis of (R)-3-methylcyclohexanone conformers. Struct Chem 33, 949–960 (2022). https://doi.org/10.1007/s11224-022-01914-2

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