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Mechanism of the acid hydrolysis of aromatic o‐carboxyamides and relative imides
Author(s) -
Nechaev P. P.,
Moiseev Yu. V.,
Vygodskii Ya. S.,
Zaikov G. E.
Publication year - 1974
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.550060204
Subject(s) - chemistry , hydrolysis , sulfuric acid , amide , dissociation (chemistry) , aqueous solution , limiting , kinetics , rate determining step , reaction mechanism , acid hydrolysis , medicinal chemistry , peptide bond , organic chemistry , polymer chemistry , catalysis , mechanical engineering , physics , quantum mechanics , engineering , enzyme
The kinetics of N ‐phenylphthalamic acid and of N ‐phenylphthalimide hydrolysis in aqueous solutions of sulfuric acid has been studied. A reaction mechanism is proposed implying that unreactive forms of the reactant appear by protonization of the amide bond at the carbonyl oxygen and by dissociation of the o‐carboxyl group ( N ‐phenylphthalamic acid). Attack of the nonprotonized amide bond by the hydroxonium ion is suggested to be the rate‐limiting step.