Experimental and theoretical approaches for identification of p-benzophenoneoxycarbonylphenyl acrylate

Abstract

The aim of this multidisciplinary study is to characterize a title compound, p-benzophenoneoxycarbonylphenyl acrylate (BPOCPA) synthesized by condensation reaction of p-acryloyloxybenzoyl chloride (ABC) with 4-hydroxybenzophenone (HBP) by means of experimental and theoretical evidences. The spectroscopic properties of the compound are experimentally examined by Fourier transformation-infrared (FTIR) spectra (in the region 400-4000 cm(-1)) and nuclear magnetic resonance (NMR) chemical shifts (with a frequency of 400 MHz). For the theoretical studies, 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, atomic charges, thermodynamic properties, (1)H and (13)C NMR chemical shifts, JCH and JCC coupling constants belonging to the BPOCPA compound are analyzed in the ground state by the way of the density functional theory (B3LYP) with the standard 6-311++G(d,p) level of theory for the first time. All the results obtained show that the calculated vibrational frequencies and chemical shifts are observed to be in good agreement with the available experimental findings. According to the comparison between experimental results and theoretical data, the calculation level chosen plays an important role in understanding of dynamics of the title compound studied in this work. The self-consistent field (SCF) energy of the molecule in six different solvent media is also analyzed at the same basis set by applying both the Onsager and Polarizable Continuum Model (PCM). It is found that the SCF energies deduced from the methods reduce with the enhancement of the solvent polarity as a consequence of the increment in the stability of the compound studied. Besides, the changes of the PCM calculations are found to be higher than those of the Onsager ones, confirming that the former method displays a more stable structure than latter model.

Keywords: B3LYP; FTIR; NMR; Onsager; PCM; p-Benzophenoneoxycarbonylphenyl acrylate.