Molecular conformational analysis, vibrational spectra, NBO analysis and first hyperpolarizability of (2E)-3-(3-chlorophenyl)prop-2-enoic anhydride based on density functional theory calculations

Abstract

The conformational behavior and structural stability of (2E)-3-(3-chlorophenyl)prop-2-enoic anhydride were investigated by using density functional theory. The optimized molecular structure, vibrational wavenumbers, corresponding vibrational assignments of (2E)-3-(3-chlorophenyl)prop-2-enoic anhydride have been investigated experimentally and theoretically. The HOMO and LUMO analysis are used to determine the charge transfer within the molecule. The stability of the molecule arising from hyperconjugative interaction and charge delocalization has been analyzed using NBO analysis. The calculated first hyperpolarizability of the title compound is 15.8×10(-30)esu, and is 121.54 times that of the standard NLO material urea and the title compound is an attractive object for future studies of nonlinear optical properties. MEP was performed by the DFT method and the predicted infrared intensities and Raman activities have also been reported.

Infrared spectrum, NBO, HOMO–LUMO, MEP and molecular docking studies (2E)-3-(3-nitrophenyl)-1-[4-piperidin-1-yl]prop-2-en-1-one

“…[73], suggesting that some multiple bond character is present. In the present case, the C@O bond length is 1.2265 Å (DFT), 1.2362 Å (XRD) and Mary et al [74] reported the C@O bond length as 1.1982 Å. In the present case the C@C bond length is 1.3426/ 1.3342 which is in agreement with the value given by Mary et al [74].…”

Molecular conformational analysis, vibrational spectra, NBO, NLO analysis and molecular docking study of bis[(E)-anthranyl-9-acrylic]anhydride based on density functional theory calculations

“…As expected, the asymmetric and symmetric C-O-C vibrations are assigned at 1105 and 1007 cm -1 theoretically for the title compound, which is in agreement with the literature [37]. For substituted cinnamic anhydrides, the C-O-C stretching modes have been reported at 1101, 1099 cm -1 (Raman), 1102, 940, 942 cm -1 (DFT) and C=C stretching modes at 1620 cm -1 (IR), 1621, 1601 cm -1 (Raman) and 1611, 1607 cm -1 (DFT) [23,24]. For 1,2,4-benzenetricarboxylic 1,2-anhydride, Arjunan et al, [38] reported In order to investigate the performance of vibrational wave numbers of the title compound, the root mean square (RMS) value between the calculated and observed wave numbers were calculated.…”

“…The calculated first hyperpolarizability of the title compound is 0.55×10 -30 e.s.u, which is comparable with the reported values of similar derivatives [12,23,24,56] and which is 4.23 times that of the standard NLO material urea (0.13×10 -30 e.s.u) [57].…”

“…The C=C groups are tilted from the anthracene rings as is evident from the torsion of the title compound was carried out at the DFT-B3LYP/6-311++G(d,p) level of theory. Similar to our previously reported conformational studies of (2E)-3-phenylprop-2-enoic anhydride[23] and its 3-chlorophenyl derivative[24], syn and anti configurations of the title compound result from the internal rotation about the -(OC)-O-(CO) linkage and are associated with the positions of the two carbonyl groups with respect to each…”

“…Therefore, it is of some importance to better understand the molecular structure of monomeric anhydrides and their electronic properties. Mary et al [23,24] reported the molecular conformational analysis, vibrational spectra of (2E)-3-phenylprop-2-enoic anhydride and (2E)-3-(3-chlorophenyl)prop-2-enoic anhydride based on density functional theory (DFT) calculations. Here, the authors report on the molecular conformational analysis and vibrational spectra of bis[(E)-anthranyl- 9-acrylic] anhydride.…”