Probing the limits of rate acceleration mediated by hydrogen bonds

COWIE, Rosalyne M., TUREGA, Simon M. and PHILP, Douglas (2006). Probing the limits of rate acceleration mediated by hydrogen bonds. Organic Letters, 8 (23), 5179-5182.

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Link to published version:: 10.1021/ol061290c


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.

Item Type: Article
Research Institute, Centre or Group: Biomolecular Sciences Research Centre
Identification Number: 10.1021/ol061290c
Depositing User: Jamie Young
Date Deposited: 30 Jun 2015 11:37
Last Modified: 30 Jun 2015 11:37

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