title: Hydrogen-deuterium exchange of aromatic amines and amides using deuterated trifluoroacetic acid.
abstract: The H-D exchange of aromatic amines and amides, including pharmaceutically relevant compounds such as acetaminophen and diclofenac, was investigated using CF3COOD as both the sole reaction solvent and source of deuterium label. The described method is amenable to efficient deuterium incorporation for a wide variety of substrates possessing both electron-donating and electron-withdrawing substituents. Best results were seen with less basic anilines and highly activated acetanilides, reflecting the likelihood of different mechanistic pathways.
authors: Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089, USA.
authors: Richard
authors: R
authors: Giles
authors: Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089, USA.
authors: Amy
authors: A
authors: Lee
authors: Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089, USA.
authors: Erica
authors: E
authors: Jung
authors: Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089, USA.
authors: Aaron
authors: A
authors: Kang
authors: Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089, USA.
authors: Kyung Woon
authors: KW
authors: Jung
keywords: Acetaminophen; Brønsted acid; CF3COOD; Electrophilic aromatic substitution; H-D exchange
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