Journal of the American Chemical Society, volume 128, issue 40, pages 13076-13083
Kinetic Effects of Hydrogen Bonds on Proton-Coupled Electron Transfer from Phenols
Martin Sjödin
1
,
Tania Irebo
1
,
Josefin E Utas
1
,
Johan Lind
1
,
Gábor Merényi
1
,
Björn Åkermark
1
,
L. HAMMARSTROM
1
Publication type: Journal Article
Publication date: 2006-09-15
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
The kinetics and mechanism of proton-coupled electron transfer (PCET) from a series of phenols to a laser flash generated [Ru(bpy)(3)](3+) oxidant in aqueous solution was investigated. The reaction followed a concerted electron-proton transfer mechanism (CEP), both for the substituted phenols with an intramolecular hydrogen bond to a carboxylate group and for those where the proton was directly transferred to water. Without internal hydrogen bonds the concerted mechanism gave a characteristic pH-dependent rate for the phenol form that followed a Marcus free energy dependence, first reported for an intramolecular PCET in Sjödin, M. et al. J. Am. Chem. Soc. 2000, 122, 3932-3962 and now demonstrated also for a bimolecular oxidation of unsubstituted phenol. With internal hydrogen bonds instead, the rate was no longer pH-dependent, because the proton was transferred to the carboxylate base. The results suggest that while a concerted reaction has a relatively high reorganization energy (lambda), this may be significantly reduced by the hydrogen bonds, allowing for a lower barrier reaction path. It is further suggested that this is a general mechanism by which proton-coupled electron transfer in radical enzymes and model complexes may be promoted by hydrogen bonding. This is different from, and possibly in addition to, the generally suggested effect of hydrogen bonds on PCET in enhancing the proton vibrational wave function overlap between the reactant and donor states. In addition we demonstrate how the mechanism for phenol oxidation changes from a stepwise electron transfer-proton transfer with a stronger oxidant to a CEP with a weaker oxidant, for the same series of phenols. The hydrogen bonded CEP reaction may thus allow for a low energy barrier path that can operate efficiently at low driving forces, which is ideal for PCET reactions in biological systems.
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1 publication, 0.71%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Sjödin M. et al. Kinetic Effects of Hydrogen Bonds on Proton-Coupled Electron Transfer from Phenols // Journal of the American Chemical Society. 2006. Vol. 128. No. 40. pp. 13076-13083.
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Sjödin M., Irebo T., Utas J. E., Lind J., Merényi G., Åkermark B., HAMMARSTROM L. Kinetic Effects of Hydrogen Bonds on Proton-Coupled Electron Transfer from Phenols // Journal of the American Chemical Society. 2006. Vol. 128. No. 40. pp. 13076-13083.
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TY - JOUR
DO - 10.1021/ja063264f
UR - https://doi.org/10.1021/ja063264f
TI - Kinetic Effects of Hydrogen Bonds on Proton-Coupled Electron Transfer from Phenols
T2 - Journal of the American Chemical Society
AU - Irebo, Tania
AU - Utas, Josefin E
AU - Lind, Johan
AU - Merényi, Gábor
AU - Sjödin, Martin
AU - Åkermark, Björn
AU - HAMMARSTROM, L.
PY - 2006
DA - 2006/09/15 00:00:00
PB - American Chemical Society (ACS)
SP - 13076-13083
IS - 40
VL - 128
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2006_Sjödin,
author = {Tania Irebo and Josefin E Utas and Johan Lind and Gábor Merényi and Martin Sjödin and Björn Åkermark and L. HAMMARSTROM},
title = {Kinetic Effects of Hydrogen Bonds on Proton-Coupled Electron Transfer from Phenols},
journal = {Journal of the American Chemical Society},
year = {2006},
volume = {128},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/ja063264f},
number = {40},
pages = {13076--13083},
doi = {10.1021/ja063264f}
}
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Sjödin, Martin, et al. “Kinetic Effects of Hydrogen Bonds on Proton-Coupled Electron Transfer from Phenols.” Journal of the American Chemical Society, vol. 128, no. 40, Sep. 2006, pp. 13076-13083. https://doi.org/10.1021/ja063264f.