TY - JOUR
T1 - Solvent isotope effect on the hydroxide-ioncatalyzed hydration of ketenes in aqueous solution
AU - Andraos, J.
AU - Chiang, Y.
AU - Eustace, S. J.
AU - Kresge, A. J.
AU - Paine, S. W.
AU - Popik, V. V.
AU - Sung, K.
PY - 1999
Y1 - 1999
N2 - 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.
AB - 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.
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U2 - 10.1139/cjc-77-4-459
DO - 10.1139/cjc-77-4-459
M3 - Article
AN - SCOPUS:0032868216
SN - 0008-4042
VL - 77
SP - 459
EP - 462
JO - Canadian Journal of Chemistry
JF - Canadian Journal of Chemistry
IS - 4
ER -