Journal of Organic Chemistry p. 3985 - 3988 (1988)
Update date:2022-08-17
Topics:
Jaeger, David A.
Clennan, Malgorzata Wegrzyn
The -OH-catalyzed hydrolyses of p-nitrophenyl acetate (1) and hexanoate (2) were performed with excess -OH on a reversed-phase liquid chromatography column of macroporous 10-μm poly(styrene-divinylbenzene) under HPLC conditions to give pseudo-first-order rate constants kψ.The maximum value of kψ1/kψ2 was <*> 25, and the reactivity difference was attributed to different rates of desorption of 1 and 2 from the polymer surface into the mobile phase, -OH was localized.The results demonstrated that a polymer-based, reversed-phase HPLC column can impart selectivity to the reactions of an ionic, inorganic reagent with neutral, organic substrates that have comparable intrinsic reactivities but different relative hydrophilic/lipophilic characters.
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