Controlling factors in the rates of oxidation of anilines and phenols by triplet methylene blue in aqueous solution

The Journal of Physical Chemistry. a
Paul R EricksonKristopher McNeill

Abstract

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 Sandros-Boltzmann 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 pKa. 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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Citations

Sep 30, 2015·Environmental Science & Technology·Marco RattiThomas B Hofstetter
Apr 14, 2016·Environmental Science & Technology·Alexandra J Salter-BlancPaul G Tratnyek
Oct 14, 2016·Environmental Science & Technology·Fernando L Rosario-Ortiz, Silvio Canonica
Mar 7, 2017·Environmental Science. Processes & Impacts·Paul G TratnyekEric J Weber
Feb 24, 2017·Environmental Science. Processes & Impacts·Ania S PavittPaul G Tratnyek
Oct 11, 2016·Environmental Science. Processes & Impacts·Kristopher McNeill, Silvio Canonica
Dec 6, 2018·Physical Chemistry Chemical Physics : PCCP·Jomana Al-Nu'airatMohammednoor Altarawneh
Sep 24, 2020·Environmental Science. Processes & Impacts·Mahsa Modiri GharehveranAmisha D Shah
Dec 24, 2018·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Frank LerescheSilvio Canonica
Jun 8, 2021·Environmental Science & Technology·Benjamin BarriosDaisuke Minakata
Apr 14, 2017·The Journal of Physical Chemistry. a·Jomana Al-Nu'airatBogdan Z Dlugogorski
Oct 17, 2017·Environmental Science & Technology·Markus SchmittKristopher McNeill
Nov 18, 2020·Environmental Science & Technology·Frank LerescheSilvio Canonica
Mar 27, 2019·Environmental Science & Technology·Nicholas C PflugKristopher McNeill
Apr 4, 2018·Environmental Science & Technology·Richie Kaur, Cort Anastasio
Jul 31, 2018·Environmental Science & Technology·Caroline A DavisElisabeth M-L Janssen
Jul 25, 2019·Environmental Science & Technology·Rachele OssolaKristopher McNeill
Jul 7, 2018·The Journal of Organic Chemistry·Gabriela F P de SouzaAirton G Salles
Dec 10, 2020·The Journal of Organic Chemistry·Vlada VershininDoron Pappo

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