Journal of the Chemical Society. Perkin transactions II p. 1327 - 1331 (1983)
Update date:2022-08-11
Topics:
Arcelli, Antonio
Concilio, Carlo
The esterolysis of 8-acetoquinoline (8-AQ) in aqueous solution in the presence of an excess of poly(diallyldimethylammonium chloride) (PDDA) or poly(ethylenimine) (PEI) was investigated at 30 deg C.In the presence of PDDA hydrolysis takes place and the polyion does not affect the rate of the reaction.In the presence of PEI the ester undergoes aminolysis and saturation kinetics are observed.The pH dependence of kobs, the apparent first-order rate constant of esterolysis, can be explained on the basis of the pH dependence of pKapp and the degree of ionization of PEI.A Broensted relationship has already been found for the aminolysis of 8-AQ with primary and secondary amines of low molecular weight.By extending the relationship to the reaction between the polymeric amino groups in PEI and 8-AQ, we can quantitatively predict the pH dependence of kobs under saturation conditions, provided that the proper values of pKapp of the amino groups are considered.
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