Spontaneous aqueous defluorination of trifluoromethylphenols: substituent effects and revisiting the mechanism

2025/01/01 by Zhefei Guo, Gynette Tremblay, Jingdan Chen +1 · 1 voice · 1 citation
Environmental Science · Pharmacology, Toxicology and Pharmaceutics · Chemistry · #Per- and polyfluoroalkyl substances research #Fluorine in Organic Chemistry #Inorganic Fluorides and Related Compounds

paper · pdf · doi:10.1039/d4em00739e

Abstract

an E1cb mechanism, driven by β-elimination. Experimental and computational results demonstrated substituent-dependent differences in reactivity, and the importance of the deprotonation of TFMPs for the hydrolysis reaction to proceed. These findings provide mechanistic insights into the complete defluorination of TFMPs and broader implications for the environmental defluorination of other PFAS.

Citations

• The Global Threat from the Irreversible Accumulation of Trifluoroacetic Acid (TFA)
• Photochemical Formation of Trifluoroacetic Acid: Mechanistic Insights into a Fluoxetine-Related Aryl-CF 3 Compound

Cited by

• Tracking Trifluoroacetate (TFA) through Time: A 78-Year Record from Archived Wines

Discussions

• New paper in Environmental Science: Processes & Impacts studying the spontaneous defluorination of some trifluoromethylphenols, led by co-first authors Zhefei Guo (PhD candidate) and Genevieve Trembl [bsky, 8 points, 1 comments]

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