Density functional theory study on the identification of 3-[(2-morpholinoethylimino)methyl]benzene-1,2-diol

This study deals with the identification of a title compound, 3-[(2-morpholinoethylimino)methyl]benzene-1,2-diol by means of quantum chemical calculations. The optimized molecular structures, vibrational frequencies and corresponding vibrational assignments, thermodynamic properties, charge analyses, nuclear magnetic resonance (NMR) chemical shifts and ultraviolet–visible (UV–vis) spectra of the title molecule in the ground state were evaluated using density functional theory (DFT) with the standard B3LYP/6-311++G(d,p) method and basis set combination for the first time. Theoretical vibrational spectra of the title compound were interpreted with the aid of normal coordinate analysis based on scaled density functional force field. The results show that the obtained optimized geometric parameters (bond lengths, bond angles and bond dihedrals) and vibrational frequencies were observed to be in good agreement with the available experimental results. Moreover, the calculations of the electronic spectra, 13C and 1H chemical shifts were compared with the experimental ones. Furthermore, we not only simulated the frontier molecular orbitals (FMO) and molecular electrostatic potential (MEP) but also determined the transition states and energy band gaps, as well. It was found that charge analyses supported the evidences of MEP. Infrared intensities and Raman activities were also reported.

Graphical abstractThe molecular electrostatic potential (MEP) is related to the electronic density and a very useful descriptor for determining sites for electrophilic attack and nucleophilic reactions as well as hydrogen-bonding interactions. In this figure, whereas electrophilic reactivity was presented by negative (red) regions, nucleophilic reactivity was shown by the positive (blue) regions of MEP. As seen from the figure, the red region was mainly delocalized on the oxygen atoms (especially O35) whereas the nucleophilic reactivity of the molecule was mainly localized on the phenyl and alkane protons. In this respect, the title compound is useful to bond both metallically and interact intermolecularly.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► This study deals with novel theoretical aspects of the title compound for the first time. ► FMO, MEP, NMR and UV–vis spectra are also performed via the computational methods. ► Theoretical data are found to be in good agreement with experimental results. ► This study carries out the novel applications in technology and industry of molecule.