DFT investigation of role of N – H⋯O and N – H⋯π interactions in the stabilization of the hydrogen bonded complexes of anisole with aromatic amines

Abstract Theoretical investigations have been performed on hydrogen (H-) bonded complexes of two aromatic amines with anisole to investigate the effect of the methyl substituent on N H⋯O and N H⋯π interactions. Natural bond orbital (NBO) and quantum theory of atoms in molecules (QTAIM) analyses were done to elucidate the nature of H- bonding. In 1:1 complexes, the total interaction energy of N-methylaniline complex is higher than that of aniline complex. The existence of bond critical point between N–H of amine and oxygen of anisole confirms weak hydrogen bonding. The energy decomposition analysis showed the role of CT in stabilizing complexes.