H Acids and Bases

The foregoing classification is of fundamental significance for the understanding of enolate chemistry. For every pair of C,H acid and base, one needs to know whether the combination effects quantitative or partial enolate formation. If deprotonation is only partial, then the unreacted substrate may represent an electrophile that can react with the enolate nucleophile. In such a case, it depends on the specific circumstances whether an enolate reacts with any remaining substrate or whether it reacts only with an added different electrophile. The occurrence of a reaction between enolate and unreacted substrate is avoided if the C,H acid is deprotonated completely with a stoichiometric amount of a sufficiently strong base. 

Komura, T., Hatsutori, K., and Imanaga, H., Acid and base properties of manganese dioxide. Rep. Asahi Glass Found. Ind. Technol., 34, 95, 1979. 

The value obtained for AI was 2.3RT ApK, where ApK corresponds to reaction rates that are equal to half the respective diffusion rates. The values of AI, obtained from Eigen s data[16] for a number of normal" (i.e., 0-H and N-H) acids and bases, are given in Table 10. These lead to values of E equal to 15.6-21.0 kcal (more probable values lie between 17 and 19 kcal). ... 

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