Hydrolysis of schiff bases 2: Intramolecular catalysis of an ortho-hydroxy group in nonionic surfactant systems

✍ Scribed by Pramila Mishra; Bijay K. Mishra; Gopa B. Behera

• Book ID: 102927955
• Publisher: John Wiley and Sons
• Year: 1992
• Tongue: English
• Weight: 747 KB
• Volume: 24
• Category: Article
• ISSN: 0538-8066
• DOI: 10.1002/kin.550240609

✦ Synopsis

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.