The structure and spectra of H-bonded complexes formed by 2-pyridone

Abstract

The self-assembly complexes formed by 2-pyridone derivatives were theoretically studied by the AM1 and DFT methods to determine their binding energies. The UV, IR, and NMR spectra of the complexes were calculated using the INDO/CIS, AM1, and B3LYP/3-21G methods, respectively. It was shown that the complexes could be formed by two monomers via double hydrogen bonding thanks to the negative binding energy. The affinity for binding was increased by substituents in the monomers. But this stimulating effect depended on the simultaneous influence of the electronic and steric effects. The first absorption bands in the UV spectra of the complexes were blue-shifted relative to that of the monomer because of their larger LUMO-HOMO energy gaps. As hydrogen bonds were formed, the N-H stretching vibrations of the monomers were weakened in the IR spectra of the complexes. And the chemical shifts of the C=C and C≡C carbon atoms were shifted downfield in the 13C NMR spectra.