Transition-state structure for the hydronium-ion-promoted hydrolysis of ±- d -glucopyranosyl fluoride

Jefferson Kar Fai Chan, Ariel Tang, Andrew J. Bennet

Research output: Contribution to journalArticle

Abstract

The transition state for the hydronium-ion-promoted hydrolysis of -d-glucopyranosyl fluoride in water has been characterized by combining multiple kinetic isotope effect measurements with theoretical modelling. The measured kinetic isotope effects for the C1-deuterium, C2-deuterium, C5-deuterium, anomeric carbon-13, and ring oxygen-18 are 1.219 ± 0.021, 1.099 ± 0.024, 0.976 ± 0.014, 1.014 ± 0.005, and 0.991 ± 0.013, respectively. The transition state for the hydronium ion reaction is late with respect to both C-F bond cleavage and proton transfer.

Original languageEnglish (US)
Pages (from-to)463-467
Number of pages5
JournalCanadian Journal of Chemistry
Volume93
Issue number4
DOIs
StatePublished - Jan 1 2014
Externally publishedYes

Keywords

  • Acid catalysis
  • Glycosides
  • Hydrolysis
  • Kinetic isotope effects
  • Mechanism

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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