Probing the limits of rate acceleration mediated by hydrogen bonds

Rosalyne M. Cowie, Simon M. Turega, Douglas Philp*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations


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 (US)
Pages (from-to)5179-5182
Number of pages4
JournalOrganic Letters
Issue number23
StatePublished - Nov 9 2006

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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