Correlation between 1H NMR chemical shifts of hydroxyl protons in n-hexanol/cyclohexane and molecular association properties investigated using density functional theory

Mario E. Flores, Toshimichi Shibue, Natsuhiko Sugimura, Hiroyuki Nishide, Ignacio Moreno-Villoslada

    Research output: Contribution to journalArticle

    6 Citations (Scopus)

    Abstract

    Association of n-hexanol molecules in cyclohexane forming clusters is studied by DFT and 1H NMR. Geometry optimization, corrected binding energies, charge distributions, charge transfer energies, and 1H NMR chemical shifts have been obtained. The calculated chemical shifts of hydroxyl protons have been correlated to experimental data obtained in the range of n-hexanol molar fraction between 0.002 and 0.2, showing that n-hexanol molecules at a molar fraction around 0.1, where well-structured hydrogen bond networks are observed, tend to form linear pentamers and hexamers. The experimental data are consistent with the continuous linear association thermodynamic model, showing a dimensionless association constant of 284.

    Original languageEnglish
    Pages (from-to)276-279
    Number of pages4
    JournalChemical Physics Letters
    Volume644
    DOIs
    Publication statusPublished - 2016 Jan 16

    Fingerprint

    Chemical shift
    Hydroxyl Radical
    cyclohexane
    Density functional theory
    chemical equilibrium
    Protons
    Nuclear magnetic resonance
    Association reactions
    density functional theory
    nuclear magnetic resonance
    protons
    charge distribution
    molecules
    Molecules
    binding energy
    Charge distribution
    charge transfer
    hydrogen bonds
    Binding energy
    Discrete Fourier transforms

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry
    • Physics and Astronomy(all)

    Cite this

    Correlation between 1H NMR chemical shifts of hydroxyl protons in n-hexanol/cyclohexane and molecular association properties investigated using density functional theory. / Flores, Mario E.; Shibue, Toshimichi; Sugimura, Natsuhiko; Nishide, Hiroyuki; Moreno-Villoslada, Ignacio.

    In: Chemical Physics Letters, Vol. 644, 16.01.2016, p. 276-279.

    Research output: Contribution to journalArticle

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    AU - Flores, Mario E.

    AU - Shibue, Toshimichi

    AU - Sugimura, Natsuhiko

    AU - Nishide, Hiroyuki

    AU - Moreno-Villoslada, Ignacio

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    AB - Association of n-hexanol molecules in cyclohexane forming clusters is studied by DFT and 1H NMR. Geometry optimization, corrected binding energies, charge distributions, charge transfer energies, and 1H NMR chemical shifts have been obtained. The calculated chemical shifts of hydroxyl protons have been correlated to experimental data obtained in the range of n-hexanol molar fraction between 0.002 and 0.2, showing that n-hexanol molecules at a molar fraction around 0.1, where well-structured hydrogen bond networks are observed, tend to form linear pentamers and hexamers. The experimental data are consistent with the continuous linear association thermodynamic model, showing a dimensionless association constant of 284.

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