DFT analysis of a key step in the cinchona-mediated organocatalytic Michael-addition of nitromethane to 1,3-diphenylpropenone

► A series of potential organocatalyst candidates was investigated by DFT analysis. ► The influence of functional groups on the activation energy was investigated. ► The significance of π stacking and H-bonding in the TS structures is pointed out. ► Nitro groups lower the activation barrier of the C-C bond formation.