Solvent isotope effect on the hydroxide-ioncatalyzed hydration of ketenes in aqueous solution

J. Andraos, Y. Chiang, S. J. Eustace, A. J. Kresge, S. W. Paine, V. V. Popik, K. Sung

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)459-462
Number of pages4
JournalCanadian Journal of Chemistry
Volume77
Issue number4
DOIs
Publication statusPublished - 1999

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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