Spectroscopic characterization and structural insights of 4-Coumarinyl-4-nitrobenzoate using vibrational and quantum chemical calculations

Abstract

The aim of the study was to synthesize 4-Coumarinyl-4-nitrobenzoate and detect its experimental and theoretical properties. 4-Coumarinyl-4-nitrobenzoate was synthesized using by the nucleophilic adduction-separation reaction of aroyl compounds. In this context 4-coumarinyl 4-nitrobenzoate compound has been characterized both experimentally and theoretically by using quantum chemical calculations and spectral techniques. Quantum chemical calculations such as the molecular geometry, geometric structure, and geometric parameters of the title compound were calculated with the 6-311G (d, p) basis set. Quantum chemical calculations of electronic properties such as energy difference between HOMO-LUMO, chemical hardness and chemical softness were made. Molecular electrostatic potential (MEP) surface of 4-Coumarinyl-4-nitrobenzoate was obtained.

Keywords

• Density Functional Theory
• MEP
• HOMO-LUMO

References

1. Bouasla, S., Amaro-Gahete J., Esquivel, D., López, M.I., Jiménez-Sanchidrián, C., Teguiche, M., Romero-Salguero, F. 2017. Coumarin derivatives solvent-free synthesis under microwave irradiation over heterogeneous solid catalysts. Molecules, 22 (12), 2072-2080.
2. Kolancılar, H. 2019. DFT Yöntemi Kullanılarak 1,3-Bis-{(2-Aminobenzoil) Amino} Propanın Teorik Hesaplamaları ve Bu Değerlerin Literatürdeki Deneysel Değerler ile Karşılaştırılması. Düzce Üniversitesi Bilim ve Teknoloji Dergisi, 7 (3), 1319-1334
3. Abdel, M.S.A., Hamed E., Saif, M., Hafez S. 2018. Binding, and thermodynamics of βcyclodextrin inclusion complexes with some coumarin laser dyes and coumarin-based enzyme substrates: a simulation study. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 92 (3), 319-327.
4. Yu, T., Zhu, Z., Bao Y., Zhao, Y., Liu, X., Zhang, H. 2017. Investigation of novel carbazolefunctionalized coumarin derivatives as organic luminescent materials. Dyes and Pigments, 147 (1), 260-269.
5. Babinski, D., Soltani, O., Frantz, D.E. 2008. Stereoselective synthesis of acetoacetate-derived enol triflates. Organic Letters, 10 (13), 2901-2904.
6. Vignale, G., Rasolt, M., 1987. Density-functional theory in strong magnetic fields. Phys. Rev. Lett. 59, 2360–2363.
7. Arunagiri, C., Arivazhagan, M., Subashini, A., Maruthaiveeran, N. 2014. Theoretical and experimental calculations, Mulliken charges and thermodynamic properties of 4-chloro-2-nitroanisole. Spectrochim. Acta Part A Mol.Biomol. Spectrosc, 131, 647-656.
8. Karakas, S,E.¸ Dereli, Ö. 2013. Molecular structure and vibrational spectra of 7-Methoxy-4-methylcoumarin by density functional method. J Mol Struct.1052, 214-20.

9. Lin-Vien, D., Fateley, WG., Grasselli, J.G., Colthup, N.B.,1991. The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules, Academic Press.
10. Fleming, J., 1976. Frontier Orbitals and Organic Chemical Reactions, John Wiley, London.
11. Lee, C., Yang, W., Parr, R.G., 1988. Local softness and chemical reactivity in the molecules CO, SCN− and H2CO. Journal of Molecular Structure: Theochem, 163, 305-313.
12. Luque, F.J., López, J.M., Orozco, M., 2000. Perspective on Electrostatic interactions of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects. Theoretical Chemistry Accounts, 103, 343-345.
13. Sebastian. S., Sundaraganesan. N., 2010. The spectroscopic (FT-IR, FT-IR gas phase, FT-Raman and UV) and NBO analysis of 4-Hydroxypiperidine by density functional method. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 75 (3), 941-952.