The effect of stabilizing enols of carboxamides by several two beta-electron-withdrawing substituents was studied with the (RRCHCONHPh)-R-1-C-2 systems. When (RRCH2)-R-1-C-2 = Meldrum's acid (MA), the solid-state structure is that of the enol (RRC)-R-1-C-2=C(OH)NHPh (7). In CDCl3 solution the structure is 7, but there may be some exchange on the NMR time scale with a tautomer. B3LYP/6-31G** calculations show a significant preference for the enol (RRC)-R-1-C-2=C(OH)NH2 (12a) ((RRC)-R-1-C-2 = MA moiety) and a small preference for (MeO2C)2C=C(OH)NHPh (11b) over the amide structures. However, solid 11 has the amide structure (MeO2C)(2)-CHCONHPh (11a). NMR spectra in CDCl3 show >90% of 11a, but a minor species, probably Ilb, is also present. In DMSO this species is not observed. The analogous dimedone-substituted anilide 10 exists both in the solid state and in solution as an enol of a ring carbonyl. Calculations show that HC(CO2Me)(3) has a lower energy than its tautomeric enol. The effects of the push-pull structures of the enols on structural and spectrometric parameters, of the beta-substituents, of the planarity of the system, of the acid derivative group (ester or anilide), and of the solvent as enol-stabilizing factors are discussed. Destabilization of the acid form contributes to the increased relative stability of the enols.