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

doi:10.1021/je900923c

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

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

6 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 language	English
Pages (from-to)	1986-1989
Number of pages	4
Journal	Journal of Chemical and Engineering Data
Volume	55
Issue number	5
DOIs	https://doi.org/10.1021/je900923c
Publication status	Published - 2010 May 13

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

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10.1021/je900923c

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Hojo, M., Ueda, T., Ike, M., Okamura, K., Sugiyama, T., Kobayashi, M., & Nakai, H. (2010). Observation by UV-visible and NMR spectroscopy and theoretical confirmation of 4-isopropyltropolonate ion, 4-isopropyltropolone (Hinokitiol), and protonated 4-isopropyltropolone in acetonitrile. Journal of Chemical and Engineering Data, 55(5), 1986-1989. https://doi.org/10.1021/je900923c

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

Research output: Contribution to journal › Article › peer-review

Hojo, M, Ueda, T, Ike, M, Okamura, K, Sugiyama, T, Kobayashi, M & Nakai, H 2010, 'Observation by UV-visible and NMR spectroscopy and theoretical confirmation of 4-isopropyltropolonate ion, 4-isopropyltropolone (Hinokitiol), and protonated 4-isopropyltropolone in acetonitrile', Journal of Chemical and Engineering Data, vol. 55, no. 5, pp. 1986-1989. https://doi.org/10.1021/je900923c

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

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

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N2 - 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.

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

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