Calculated amide/enol of amide energy differences for several interesting amide systemsElectronic supplementary information (ESI) available: optimised structures of various conformers. See http://www.rsc.org/suppdata/cc/b0/b006216m/
Abstract
The calculated pKEnol values for the enols of amides Me2CHCON(Me)Ph and XCH2CH(NH2)CONHMe (X = H,OH) are lower by only 1.1–2.7 units than that of acetamide, and therefore these enols should not display unusual stability.