Rate and Equilibrium Studies of the Reaction of Oxyanions with 2-Phenyloxazol-5(4H)-one

DOI: 10.1039/P29860000163

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 163 - 168 (1986)

Update date:2022-08-03

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Authors:

Chrystiuk, Edwin

Jusoh, Adelina

Santafianos, Dino

Williams, Andrew

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Article abstract of DOI:10.1039/P29860000163

Equilibrium constants for the reaction of phenoxide ions with 2-phenyloxazol-5(4H)-one at 25 deg C and 1M ionic strength obey a Broensted relationship (log k_OH/k_ArO = log K' = -173pK^ArOH - 15.81) and are not subject to steric effects from ortho-substituents.Both forward and reverse rate parameters exhibit steric effects, and the Broensted equations for meta- and para-substituted species are log k_OH = -0.81 pK^ArOH + 9.75, and log k_ArO = 0.95pK^ArOH - 6.40.There is no break in the Broensted line in the region of pK^ArOH 5-11, consistent with a single transition-state.An upward deviation exists for oxyanions with low basicity (pK^XOH < 5); one of these oxyanions, betaine, has a solvent deuterium oxide isotope effect for its reaction with the oxazolone greater than 2, consistent with a general base mechanism for attack for these species.The results for nucleophilic attack of phenolate anions are in agreement with a concerted displacement at the carbonyl group.

Full text of DOI:10.1039/P29860000163

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