Acceleration of proton exchange between octanol and water by 2,4-dinitrophenol determined by 1H-NMR spectrometry a new model for proton transfer in a hydrophobic environment |
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Authors: | Hiroshi Terada Keiko Shirakawa Fujio Kametani Kenichi Yoshikawa |
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Affiliation: | 1. Faculty of Pharmaceutical Sciences, University of Tokushima, Shomachi-1, Tokushima 770 Japan;2. College of General Education, University of Tokushima, Minami Josanjima, Tokushima 770 Japan |
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Abstract: | The rate of proton transfer between the octanol -OH group and water dissolved in octanol after partition equilibrium was determined by 1H-NMR spectrometry. The rate was found to depend on the pH of the aqueous phase, being minimal at about pH 11. The uncoupler of oxidative phosphorylation 2,4-dinitrophenol at about 10?3 M accelerated proton transfer several-fold. Its effect was shown to depend on the concentration of the neutral form of 2,4-dinitrophenol in the octanol phase, irrespective of the pH of the aqueous phase. This effect is suggested to be based on the catalytic action of the phenolic -OH group in 2,4-dinitrophenol. The importance of this effect in the uncoupling action of 2,4-dinitrophenol is discussed. |
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Keywords: | NMR Proton transfer Uncoupler Oxidative phosphorylation 2,4-Dinitrophenol SF6847 FCCP |
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