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.
Full text not available from this repository.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 |
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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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