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Probing the limits of rate acceleration mediated by hydrogen bonds

Research output: Contribution to journalArticle

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Author(s)

R M Cowie, S M Turega, Douglas Philp

School/Research organisations

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.

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

    Research areas

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

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