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Reactions of salts of deuterated benzenecarboxylic acids
Author(s) -
Ratuský J.
Publication year - 1970
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590060203
Subject(s) - carbanion , deuterium , chemistry , benzene , hydrogen–deuterium exchange , ring (chemistry) , hydrogen , reaction mechanism , proton , intermolecular force , ionic bonding , medicinal chemistry , ion , organic chemistry , catalysis , molecule , nuclear physics , physics
The course of transcarboxylation reactions of potassium salts of deuterated benzenecarboxylic acids was investigated. During the reaction rapid random exchange of hydrogen atoms of the benzene ring for deuterium takes place. The probable mechanism of this exchange, which involves the liberation of protons from the benzene ring and the formation of carbanions, is proposed. The mechanism of the deuterium for hydrogen exchange is in agreement with the intermolecular ionic mechanism of the transcarboxylation reaction itself since the formation of carbanions via liberation of protons is a part of this reaction.