Observation by UV-visible and NMR spectroscopy and theoretical confirmation of 4-isopropyltropolonate ion, 4-isopropyltropolone (Hinokitiol), and protonated 4-isopropyltropolone in acetonitrile

Masashi Hojo, Tadaharu Ueda, Michitaka Ike, Kei Okamura, Taku Sugiyama, Masato Kobayashi, Hiromi Nakai

    Research output: Contribution to journalArticle

    5 Citations (Scopus)

    Abstract

    Protonated 4-isopropyltropolone (H2L+) was produced by the addition of methanesulfonic or trifluoromethanesulfonic acid to 4-isopropyltropolone (hinokitiol: HL) dissolved in a protophobic aprotic solvent, acetonitrile, with poor solvation of anions and cations. The formation was confirmed by UV-visible and 13C NMR spectroscopy as well as theoretical calculations using the Gaussian03 quantum chemistry package. The 13C chemical shifts of all C-atoms in the seven-membered ring were properly assigned for H2L+ and HL as well as for the deprotonated species, L-. The influence of residual water in the organic solvent was regarded as negligible because such a water is in the "dihydrogen ether" condition.

    Original languageEnglish
    Pages (from-to)1986-1989
    Number of pages4
    JournalJournal of Chemical and Engineering Data
    Volume55
    Issue number5
    DOIs
    Publication statusPublished - 2010 May 13

    Fingerprint

    Acetonitrile
    Nuclear magnetic resonance spectroscopy
    Ions
    Quantum chemistry
    Solvation
    Chemical shift
    Organic solvents
    Water
    Ethers
    Negative ions
    Positive ions
    Ether
    Atoms
    Anions
    Acids
    Cations
    beta-thujaplicin
    acetonitrile

    ASJC Scopus subject areas

    • Chemistry(all)
    • Chemical Engineering(all)

    Cite this

    Observation by UV-visible and NMR spectroscopy and theoretical confirmation of 4-isopropyltropolonate ion, 4-isopropyltropolone (Hinokitiol), and protonated 4-isopropyltropolone in acetonitrile. / Hojo, Masashi; Ueda, Tadaharu; Ike, Michitaka; Okamura, Kei; Sugiyama, Taku; Kobayashi, Masato; Nakai, Hiromi.

    In: Journal of Chemical and Engineering Data, Vol. 55, No. 5, 13.05.2010, p. 1986-1989.

    Research output: Contribution to journalArticle

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    abstract = "Protonated 4-isopropyltropolone (H2L+) was produced by the addition of methanesulfonic or trifluoromethanesulfonic acid to 4-isopropyltropolone (hinokitiol: HL) dissolved in a protophobic aprotic solvent, acetonitrile, with poor solvation of anions and cations. The formation was confirmed by UV-visible and 13C NMR spectroscopy as well as theoretical calculations using the Gaussian03 quantum chemistry package. The 13C chemical shifts of all C-atoms in the seven-membered ring were properly assigned for H2L+ and HL as well as for the deprotonated species, L-. The influence of residual water in the organic solvent was regarded as negligible because such a water is in the {"}dihydrogen ether{"} condition.",
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    AU - Hojo, Masashi

    AU - Ueda, Tadaharu

    AU - Ike, Michitaka

    AU - Okamura, Kei

    AU - Sugiyama, Taku

    AU - Kobayashi, Masato

    AU - Nakai, Hiromi

    PY - 2010/5/13

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    AB - Protonated 4-isopropyltropolone (H2L+) was produced by the addition of methanesulfonic or trifluoromethanesulfonic acid to 4-isopropyltropolone (hinokitiol: HL) dissolved in a protophobic aprotic solvent, acetonitrile, with poor solvation of anions and cations. The formation was confirmed by UV-visible and 13C NMR spectroscopy as well as theoretical calculations using the Gaussian03 quantum chemistry package. The 13C chemical shifts of all C-atoms in the seven-membered ring were properly assigned for H2L+ and HL as well as for the deprotonated species, L-. The influence of residual water in the organic solvent was regarded as negligible because such a water is in the "dihydrogen ether" condition.

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