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.
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.
|Research Institute, Centre or Group:||Biomolecular Sciences Research Centre|
|Depositing User:||Jamie Young|
|Date Deposited:||30 Jun 2015 11:37|
|Last Modified:||30 Jun 2015 11:37|
Actions (login required)
Downloads per month over past year