Abstract: 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 deprotonated, but a stereochemical assignment cannot be made. The order of acidity is aldehyde> amide> ester based on the MO calculations, ...
