10327-01-2Relevant academic research and scientific papers
Solvent isotope effect on the hydroxide-ioncatalyzed hydration of ketenes in aqueous solution
Andraos,Chiang,Eustace,Kresge,Paine,Popik,Sung
, p. 459 - 462 (2007/10/03)
Five ketenes, phenyl(ethyl)ketene, phenyl(methylthio)ketene, diphenylketene, pentafluorophenylketene, and 1-naphthylketene, were generated flash photolytically and solvent isotope effects (H2O vs. D2O) on their hydroxide-ioncatalyzed hydration in aqueous solution were determined. The values obtained are all weakly reverse and closely similar (k(HO)/k(DO) = 0.76-0.97), as expected for these fast, hydroxide-ion-consuming reactions, known to proceed by nucleophilic attack of hydroxide on the ketene carbonyl group. The characteristic magnitude of these isotope effects should prove useful in identifying new examples of this reaction.
