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. Author manuscript; available in PMC: 2018 Jul 1.
Published in final edited form as: Synlett. 2017 Mar 10;28(12):2407–2421. doi: 10.1055/s-0036-1588778

Chart 5.

Chart 5

A comparison of the thermodynamic (pKa) and kinetic acidity (kHO for hydroxide catalyzed deprotonation) of neutral and cationic carbon acids. The paired carbon acids show similar pKas, and a significantly larger rate constant kHO for deprotonation of the cationic acid.