Basicity of the polydentate captodative aminoenones. Ab initio, DFT, and FTIR study

Electron donating ability of the oxygen, nitrogen, and carbon atoms of captodative aminoenones R'CH = C(NR2)EWG, EWG = CHO, C(O)Me, C(O)CF3, C(O)Ph was investigated using ab initio and Density Functional Theory (DFT) calculations, Natural Bond Orbital (NBO) analysis, and Fourier Transform InfraRed (FTIR) spectroscopy. The influence of both electron withdrawing group (EWG) and double bond substituents on the proton affinity of the basic centers, orbital interaction, as well as resonance stabilization energies between heteroatoms and double bonds are discussed. The results obtained are critically compared with the push-pull aminoenones. The comparison of experimental values Delta nu OH and theoretical values of H-bonding energy was used to determine the H-complex type of aminoenone with phenol and the H-bond strength. Copyright (C) 2016 John Wiley & Sons, Ltd.