mechanism | organic synthesis | chemical biology
Radical-Trapping Antioxidants (aka RTAs)
Autoxidation is the free radical chain reaction that leads to the degradation of all hydrocarbons - from plastics, rubbers, lubricants and (bio)fuels to the lipids of the membranes of living cells. The key propagating radicals of the chain reactions are peroxyl radicals, which are the targets of the radical-trapping antioxidants (RTAs) that are added to hydrocarbon-based products as preservatives. We study how the various classes of RTA commonly incorporated into hydrocarbon-based products work (e.g. phenols, diphenylamines, hindered amines and sulfurized olefins) and make use of this knowledge to design new compounds/reactivity to help optimize humanity's usage of both petroleum-derived and bio-based hydrocarbons.
Check out some representative work from our lab:
Interrupted Homolytic Substitution Enables Organoboron Compounds to Inhibit Radical Chain Reactions Rather than Initiate Them
Zijun Wu, Robynne Vlaming, Michael Donohoe & Derek A. Pratt*
Journal of the American Chemical Society, 2024, 146, ASAP Article
Autoxidation vs. Antioxidants - The Fight for Forever
Julian Helberg & Derek A. Pratt*
Chemical Society Reviews 2021, 50, 7343-7358
Temperature-Dependence of Radical-Trapping Activity of Phenoxazine, Phenothiazine and their Aza-Analogues Clarifies the Way Forward for New Antioxidant Design
Jia-Fei Poon, Luke A. Farmer, Evan A. Haidasz & Derek A. Pratt*
Chemical Science 2021, 12, 11065-11079
Persistent Quinone Methide Dimers Lacking Labile H-Atoms Are Surprisingly Excellent Radical-Trapping Antioxidants
Mark A. R. Raycroft, Jean-Philippe R. Chauvin, Matthew S. Galliher, Kevin J. Romero, Corey R. J. Stephenson* & Derek A. Pratt*
Chemical Science 2020, 11, 5676-5689
Inhibition of Hydrocarbon Autoxidation by Nitroxide-Catalyzed Cross-Dismutation of Hydroperoxyl and Alkylperoxyl Radicals
Kareem A. Harrison, Evan A. Haidasz, Markus Griesser & Derek A. Pratt*
Chemical Science 2018, 9, 6068-6079
Recent Insights on Hydrogen Atom Transfer in the Inhibition of Hydrocarbon Autoxidation
Jia-Fei Poon & Derek A. Pratt*
Accounts of Chemical Research 2018, 51, 1996-2005
