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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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.

Item Type:	Article
Research Institute, Centre or Group - Does NOT include content added after October 2018:	Biomedical Research Centre
Identification Number:	https://doi.org/10.1021/ol061290c
Page Range:	5179-5182
Depositing User:	Jamie Young
Date Deposited:	30 Jun 2015 11:37
Last Modified:	18 Mar 2021 18:45
URI:	https://shura.shu.ac.uk/id/eprint/10029

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