Solvent Effects On Alkaline Hydrolysis Of N-Benzylphthalimide In Mixed Water-Acetonitrile And Mixed Water-N,N-Dimethylformamide

The nucleophilic second-order rate constant (kappa(OH)) for the reaction of OH- with N-benzylphthalimide appears to follow a reaction mechanism similar to that for reactions of OH with phthalimide and its N-alkylphthalimides. The rate of hydrolysis reveals an insignificant contribution of water-cata...

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Bibliographic Details
Main Authors: Ariffin, Azhar, Khan, M.N., Ye, C.M.
Format: Article
Published: 2005
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Online Access:http://eprints.um.edu.my/8046/
http://cat.inist.fr/?aModele=afficheN&cpsidt=17165667
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Summary:The nucleophilic second-order rate constant (kappa(OH)) for the reaction of OH- with N-benzylphthalimide appears to follow a reaction mechanism similar to that for reactions of OH with phthalimide and its N-alkylphthalimides. The rate of hydrolysis reveals an insignificant contribution of water-catalysed cleavage of NBPT compared with its hydroxide ion catalysed reaction. The observed pseudo first-order rate constant, kappa(obs), for alkaline hydrolysis of NBPT decreases with increase in the content of organic cosolvents (up to 70%, nu/nu) in mixed water-CH3CN and water-DMF solvents.