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 language | English (US) |
|---|---|
| Pages (from-to) | 463-467 |
| Number of pages | 5 |
| Journal | Canadian Journal of Chemistry |
| Volume | 93 |
| Issue number | 4 |
| DOIs | |
| State | Published - 2014 |
| Externally published | Yes |
Keywords
- Acid catalysis
- Glycosides
- Hydrolysis
- Kinetic isotope effects
- Mechanism
ASJC Scopus subject areas
- Catalysis
- General Chemistry
- Organic Chemistry