Synthesis and computational studies on a coumarin derivative: 4-chloromethyl coumarin-7-yl-methacrylate

In this article, we report the synthesis, X-ray structure determination, geometric parameters, vibrational frequencies, NMR, and UV spectra of a coumarin derivative titled 4-chloromethyl coumarin-7-yl-methacrylate (CCMA). In the study, the theoretical vibrational frequencies, NMR and UV spectra, and optimized geometric parameters were computed by using density functional theory with the hybrid methods B3LYP/6-31 + G(d,p) basis set. The optimized geometric parameters, vibrational frequencies, and H-1 and C-13 NMR chemical shifts values were contrasted with experimental values of the title molecule. The theoretical vibrational frequencies were found in concordance with the matching experimental data. The electronic properties of the molecule were studied using the molecular frontier orbital energies, ESP surfaces, the natural bond orbital (NBO), and nonlinear optical (NLO) properties. The study findings show that the molecule has nucleophilic regions around O atoms and the transition from the ground state to the first excited state with the electronic absorption peaks at 318.19 nm in gas. In this study, the remarkable electron delocalization occurred between the donor (C4-C5) anti bond and acceptor (C6-C9) anti bond with 249.60 kcal/mol stabilization energy in the title molecule. Calculated NLO parameters show that CCMA can be used as the NLO material. (C) 2022 Elsevier B.V. All rights reserved.