Methyl Anion Affinities of the Canonical Organic Functional Groups.

Calculated methyl anion affinities are known to correlate with experimentally determined Mayr parameters for individual organic functional group classes but not between neutral and cationic organic electrophiles. We demonstrate that methyl anion affinities calculated with a solvation model (MAA*) give a linear correlation with Mayr parameters for a broad range of functional groups. Methyl anion affinities (MAA*), plotted on the log scale of Mayr , provide insights into the full range of electrophilicity of organic functional groups. On the Mayr scale, the electrophilicity toward the methyl anion spans 180 orders of magnitude.