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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 18, Number 12
BKCSDE 18(12)
December 20, 1997 

Reactions in Surfactant Solutions(Ⅴ): Dephosphorylation of p-Nitrophenyldiphenylphosphinate by Benzimidazole Catalyzed with Ethyltri-n-octylammonium Bromide
Young-Seuk Hong*, Jeong-Geun Lee, Hyun-Mook Kim
The phase-transfer reagent (PTC), ethyl tri-n-octylammonium bromide (ETABr), strongly catalyzes the reaction of p-nitrophenyldiphenylphosphinate (p-NPDPIN) with benzimidazole (BI) and its anion (BI-). In ETABr solutions, the dephosphorylation reactions exhibit higer than first order kinetics with respect to the nucleophile, BI, and ETABr, suggesting that reactions are occuring in small aggregates of the three species including the substrate, whereas the reaction of p-NPDPIN with OH- is not catalyzed by ETABr. This behavior for the drastic rate-enhancement of the dephosphorylation is refered as 'aggregation complex model' for reactions of hydrophobic organic phosphinates with benzimidazole in hydrophobic quarternary ammonium salt solutions.
1260 - 1264
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