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  4. Controlling Factors in the Rates of Oxidation of Anilines and Phenols by Triplet Methylene Blue in Aqueous Solution
 
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research article

Controlling Factors in the Rates of Oxidation of Anilines and Phenols by Triplet Methylene Blue in Aqueous Solution

Erickson, Paul R.
•
Walpen, Nicolas
•
Guerard, Jennifer J.  
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2015
The Journal of Physical Chemistry A

Anilines and phenols are structurally similar compound classes that both are susceptible to oxidation by excited state triplet sensitizers but undergo oxidation by different mechanisms. To gain an understanding of the factors that control the rate of oxidation of anilines and phenols by triplet excited states, a kinetic study was performed on the oxidation of substituted anilines and phenols by methylene blue. The rate constants of one-electron transfer from anilines to triplet state methylene blue and their dependence on the reaction free energy are well fit to a SandrosBoltzmann model. The observed rate constants are also well modeled when aniline oxidation potentials derived computationally are used. For phenols, the proton-coupled electron transfer rate constants were found to correlate primarily with O-H bond dissociation free energy and secondarily with phenol pK(a center dot) Rate constants for phenols could be modeled using computed bond dissociation free energies. These results provide a basis for predicting aniline and phenol oxidation rates, which could be valuable, for example, in assessing the likely persistence and fate of aniline- and phenol-based aqueous environmental pollutants.

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Type
research article
DOI
10.1021/jp511408f
Web of Science ID

WOS:000352331600010

Author(s)
Erickson, Paul R.
•
Walpen, Nicolas
•
Guerard, Jennifer J.  
•
Eustis, Soren E.
•
Arey, J. Samuel  
•
McNeill, Kristopher
Date Issued

2015

Publisher

American Chemical Society

Published in
The Journal of Physical Chemistry A
Volume

119

Issue

13

Start page

3233

End page

3243

Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LMCE  
Available on Infoscience
March 4, 2015
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/112142
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