Journal of the Chemical Society. Perkin transactions II p. 163 - 168 (1986)
Update date:2022-08-03
Topics:
Chrystiuk, Edwin
Jusoh, Adelina
Santafianos, Dino
Williams, Andrew
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 kOH/kArO = log K' = -173pKArOH - 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 kOH = -0.81 pKArOH + 9.75, and log kArO = 0.95pKArOH - 6.40.There is no break in the Broensted line in the region of pKArOH 5-11, consistent with a single transition-state.An upward deviation exists for oxyanions with low basicity (pKXOH < 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.
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