| Autor: |
Chan J; Chemistry Department, Simon Fraser University , 8888 University Drive, Burnaby, British Columbia V5A 1S6, Canada., Sannikova N, Tang A, Bennet AJ |
| Jazyk: |
angličtina |
| Zdroj: |
Journal of the American Chemical Society [J Am Chem Soc] 2014 Sep 03; Vol. 136 (35), pp. 12225-8. Date of Electronic Publication: 2014 Aug 19. |
| DOI: |
10.1021/ja506092h |
| Abstrakt: |
We report that the SN2 reaction of α-d-glucopyranosyl fluoride with azide ion proceeds through a loose (exploded) transition-state (TS) structure. We reached this conclusion by modeling the TS using a suite of five experimental kinetic isotope effects (KIEs) as constraints for the calculations. We also report that the anomeric (13)C-KIE is not abnormally large (k12/k13 = 1.024 ± 0.006), a finding which is at variance with the previous literature value (Zhang et al. J. Am. Chem. Soc. 1994, 116, 7557). |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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