Small Molecule Catalysis of Proton Transfer at Carbon

It has been proposed that part or all of the intrinsic barrier for deprotonation of a-carbonyl carbon is associated with the requirement for solvation of the negatively charged oxygen of the enolate anion [80]. However, the observation of small intrinsic barriers for deprotonation of oxygen acids by electronegative bases to form solvated anions [31] suggests that the requirement for a similar solvation of enolate anions should not make a large contribution to the intrinsic barrier for deprotonation of a-carbonyl carbon. 

Small Molecule Catalysis of Proton Transfer at Carbon 

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