Probing the limits of rate acceleration mediated by hydrogen bonds

Rosalyne M. Cowie; Simon M. Turega; Douglas Philp

doi:10.1021/ol061290c

Probing the limits of rate acceleration mediated by hydrogen bonds

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

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

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 language	English (US)
Pages (from-to)	5179-5182
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	23
DOIs	https://doi.org/10.1021/ol061290c
State	Published - Nov 9 2006

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol061290c

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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.",

author = "Cowie, {Rosalyne M.} and Turega, {Simon M.} and Douglas Philp",

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Probing the limits of rate acceleration mediated by hydrogen bonds

Abstract

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