Dipole-Stabilized Carbanions in the Gas Phase

Article abstract of DOI:10.1021/ja00341a007

The energetics, structures, and reactivities of several dipole-stabilized carbanions from formamides, aldehydes, and formamidines have been examined by ICR mass spectrometry and by MNDO calculations.Experimentally in the amides, only one of the alkyl groups on nitrogen appears to be deprotonate, but a stereochemical assignment cannot be made.The order of acidity is aldehyde > amide > ester based on the MO calculations, indicating that the external dipole moment of these carbon acids is not a good measure of acidity.The acidities folow the inductive ordering, based on ?_I constants.