The gas-phase proton affinities (PAs) of a series of novel diamidocarbenes (DACs) were assessed and compared to various imidazolylidene-based N-heterocyclic carbenes (NHCs) through experimental and computational methods. Apart from a perfluorinated-phenyl derivative (PA= 233 kcal/mol), the calculated and measured PAs for a range of DACs (256– 261 kcal/mol) were comparable to those of the NHCs (260–266 kcal/mol). Proton transfer ...