Experimental and theoretical studies on the identification of p-biphenyloxycarbonylphenyl acrylate

This study presents the identification of a title compound, p-biphenyloxycarbonylphenyl acrylate by means of experimental and theoretical evidences. The spectroscopic properties of the compound were experimentally investigated by Fourier transformation-infrared spectra (in the region 400–4000 cm−1) and nuclear magnetic resonance (NMR) chemical shifts (with a frequency of 400 MHz). Moreover, the optimized molecular structures, vibrational frequencies including infrared intensities and Raman activities, corresponding vibrational spectra interpreted with the aid of normal coordinate analysis based on scaled density functional force field, thermodynamic properties, atomic charges and ultraviolet–visible (UV–vis) spectra were analyzed utilizing ab initio Hartree–Fock (HF) and Density Functional Theory (B3LYP) methods at 6-31G(d,p) calculation level. It was found that the vibrational frequencies and chemical shifts obtained were shown to have a good agreement with available experimental results. We not only simulated frontier molecular orbitals (FMO) and molecular electrostatic potential (MEP) but also evaluated the transition state and energy band gap clearly.

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 localized on the vicinity of oxygen atoms. On the other hand, although the blue region was not seen clearly the nucleophilic reactivity of the molecule was localized on the hydrogen atoms (especially vinyl group). In this respect, the compound is useful to both bond metallically and interact intermolecularly.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► This study deals with novel theoretical aspects and novel applications of the molecule. ► Vibrational frequencies and 1H chemical shifts are experimentally observed. ► FMO, MEP and UV–vis spectra are also performed via quantum computational methods. ► Theoretical data are found to be in good agreement with experimental results. ► This study shows the way to future studies of the molecule.