Kinetics and mechanism of intramolecular Carboxylic Acid participation in the hydrolysis of N-Methoxyphthalamic Acid

The rate of formation and disappearance of phthalic anhydride (PAn) intermediate in the aqueous cleavage of N-methoxyphthalamic acid (NMPA) under acidic pH was studied spectrophotometrically in mixed CH3CN-H2O solvents. The rate of formation of PAn from NMPA is almost independent of the change in ac...

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Bibliographic Details
Main Authors: Ariffin, Azhar, Khan, M.N.
Format: Article
Language:en
Published: 2003
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Online Access:http://eprints.um.edu.my/8040/1/Khan-2003-Kinetics_and_mechani.pdf
http://eprints.um.edu.my/8040/
http://pubs.rsc.org/en/content/articlepdf/2003/ob/b300662j
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Summary:The rate of formation and disappearance of phthalic anhydride (PAn) intermediate in the aqueous cleavage of N-methoxyphthalamic acid (NMPA) under acidic pH was studied spectrophotometrically in mixed CH3CN-H2O solvents. The rate of formation of PAn from NMPA is almost independent of the change in acetonitrile content from 20 to 70% v/v in mixed aqueous solvents. The rate constants for the formation of PAn from NMPA are similar to10-fold smaller than the corresponding rate constants for the formation of PAn from o-carboxybenzohydroxamic acid (OCBA). These observations are ascribed to the consequence of the occurrence of slightly different mechanisms in these reactions.