Welcome to LookChem.com Sign In|Join Free

Article Doi

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

Topics:

Authors:

Chrystiuk, EdwinChrystiuk, Edwin

Jusoh, AdelinaJusoh, Adelina

Santafianos, DinoSantafianos, Dino

Williams, AndrewWilliams, Andrew

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

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 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.

View More

Products guided by the article

Product name:Glycine, N-benzoyl-, 4-acetylphenyl ester

Cas No:29736-18-3

29736-18-3

R&D Labs maybe for 29736-18-3

Relevant to this article

Hot Product