Transition-state structure for the quintessential SN2 reaction of a carbohydrate: Reaction of α-glucopyranosyl fluoride with azide ion in Water

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

Research output: Contribution to journalArticle

Abstract

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 13C-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).

Original languageEnglish (US)
Pages (from-to)12225-12228
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number35
DOIs
StatePublished - Sep 3 2014

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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