Artificial receptors involved in enolization and pK(a) shifts.
Abiotic receptors used to enolize carbonyl compounds or to shift substrate pK(a) values are reviewed. These systems exhibit disparate frameworks and several approaches to binding and anion stabilization. Detailed emphasis is placed on a bicyclic cyclophane that induces pK(a) shifts in active methylene compounds through NH-pi hydrogen bonding with the resultant enolates.
Snowden
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TS
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712, USA.
Bisson
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AP
Anslyn
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EV
D002384:Catalysis; D003505:Cyclodextrins / Q000737:chemistry; D004988:Ethers, Cyclic / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D018716:Molecular Mimicry; D010751:Phosphopyruvate Hydratase / Q000737:chemistry*
D003505:Cyclodextrins; D004988:Ethers, Cyclic; D010751:Phosphopyruvate Hydratase