Probing the limits of rate acceleration mediated by hydrogen bonds

R M Cowie, S M Turega, Douglas Philp

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

A simple receptor and substrate are used to probe the relationship between transition-state charge and the level of rate acceleration that can be created by stabilizing the transition state through hydrogen bonding. Pericyclic reactions are accelerated less than 2-fold by the receptor, whereas a conjugate addition reaction is accelerated more than 30-fold. Therefore, substrate polarization by hydrogen bonding would only appear to be effective for reactions that generate significant charge at the transition state.

Original languageEnglish
Pages (from-to)5179-5183
Number of pages4
JournalOrganic Letters
Volume8
Issue number23
DOIs
Publication statusPublished - 9 Nov 2006

Keywords

  • DIELS-ALDER REACTION
  • ANTIBODY-CATALYSIS
  • MACROPHOMATE SYNTHASE
  • CHORISMATE MUTASE
  • CYCLOADDITION REACTION
  • DIPOLAR CYCLOADDITION
  • REACTION-MECHANISM
  • RECOGNITION
  • REARRANGEMENT
  • BIOSYNTHESIS

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