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Carboxylic Acid Catalyzed Keto‐Enol Tautomerizations in the Gas Phase
Author(s) -
da Silva Gabriel
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201003530
Subject(s) - enol , ketone , carboxylic acid , gas phase , catalysis , chemistry , hydrogen , photochemistry , phase (matter) , reaction mechanism , mechanism (biology) , organic chemistry , physics , quantum mechanics
Long live the ketone! Carboxylic acids are shown to directly participate in gas‐phase keto–enol tautomerizations that occur through a novel chemically activated double‐hydrogen‐shift (DHS) mechanism. This mechanism decreases the reaction barrier by an order of magnitude, and is predicted to reduce the lifetimes of the atmospheric enol forms to approximately one hour.