Methyl Anion Affinities of the Canonical Organic Functional Groups
Aaron Mood, Mohammadamin Tavakoli, Eugene S. Gutman, Dora Kadish, Pierre Baldi, David L. Van Vranken
Abstract
Calculated methyl anion affinities are known to correlate with experimentally determined Mayr E 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 E parameters for a broad range of functional groups. Methyl anion affinities (MAA*), plotted on the log scale of Mayr E, provide insights into the full range of electrophilicity of organic functional groups. On the Mayr E scale, the electrophilicity toward the methyl anion spans 180 orders of magnitude.
Topics & Concepts
AffinitiesChemistryElectrophileCationic polymerizationSolvationIonDensity functional theoryBinding affinitiesComputational chemistryStereochemistryOrganic chemistryReceptorBiochemistryCatalysisChemical Reaction MechanismsAdvanced Chemical Physics StudiesSpectroscopy and Quantum Chemical Studies