Experimental and ab initio computational studies on 4-(1H-benzo[d]imidazol-2-yl)-N,N-dimethylaniline

Abstract

The title molecule, 4-(1H-benzo[d]imidazol-2-yl)-N,N-dimethylaniline (C15H15N3), was prepared and characterised by 1H-NMR, 13C-NMR, IR and single-crystal X-ray diffraction. The molecular geometry, vibrational frequencies and gauge including atomic orbital (GIAO) 1H- and 13C-NMR chemical shift values of the title compound in the ground state have been calculated using the Hartree–Fock (HF) and density functional theory (DFT) methods with 6–31G(d) basis sets, and compared with the experimental data. The calculated results show that the optimised geometries can well reproduce the crystal structural parameters and the theoretical vibrational frequencies, and 1H- and 13C-NMR chemical shift values show good agreement with experimental data. To determine conformational flexibility, the molecular energy profile of the title compound was obtained by semi-empirical (AM1) calculations with respect to the selected torsion angle, which was varied from −180° to +180° in steps of 5°. The energetic behaviour of the title compound in solvent media was examined using the B3LYP method with the 6–31G(d) basis set by applying the Onsager and the Polarizable Continuum Model (PCM). In addition, the molecular electrostatic potential (MEP), frontier molecular orbitals (FMO) analysis and thermodynamic properties of the title compound were investigated using theoretical calculations.