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Hydrolysis of schiff bases 2: Intramolecular catalysis of an ortho‐hydroxy group in nonionic surfactant systems
Author(s) -
Mishra Pramila,
Mishra Bijay K.,
Behera Gopa B.
Publication year - 1992
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.550240609
Subject(s) - chemistry , intramolecular force , catalysis , hydrolysis , reactivity (psychology) , pulmonary surfactant , nucleophile , naphthalene , schiff base , molecule , medicinal chemistry , organic chemistry , photochemistry , polymer chemistry , medicine , biochemistry , alternative medicine , pathology
The rates of hydrolysis of N ‐(2&4‐hydroxybenzylidene)‐2‐aminobenzothiazoles has been studied in the pH range 4–13 in a 10% dioxane‐water system and in various nonionic surfactant systems. The reaction is found to be due to water mediated intramolecular general base catalysis within the pH range 4.0 to 12.0 and due to nucleophilic catalysis beyond pH 12.0. A ten membered intermediate facilitating transannular attack of a water molecule on the methine carbon forming a naphthalene type transition state has been proposed. The reactivity difference in water and nonionic surfactants has been explained by a suitable entrapment model.