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Intramolecular general base catalysis exerted by the carboxilate group in the spontaneous dehydration of the carbinolamine formed from benzoylformic anion and hydroxylamine at early values of pH
Author(s) -
Calzadilla M.,
Malpica A.,
Mejias I.
Publication year - 2007
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1180
Subject(s) - chemistry , hydroxylamine , dehydration , intramolecular force , carboxylate , base (topology) , oxime , catalysis , ion , medicinal chemistry , polymer chemistry , organic chemistry , biochemistry , mathematical analysis , mathematics
Data obtained from the reaction of oxime formation from benzoylformic anion lead to the suggestion that the spontaneous dehydration observed after pH ∼ 5.0, proceeds through a transition state in which an intramolecular general base catalysis is exerted by the carboxylate group. Copyright © 2007 John Wiley & Sons, Ltd.