Investigation molecular and radical structures of three-carboxyfuran by DFT and EPR on gas-phase

Abstract

Three-carboxyfuran (C5H4O3) is a member of organic compounds. The structure, radical properties, and Electron paramagnetic resonance (EPR) parameters of this organic compound were studied using computational methods. Conformational analysis, which examines the potential energy surface of the molecule in order to determine the stable structure of the molecule, was performed with the Spartan program. Then the conformations obtained as a result of this calculation were optimized by using B3LYP functional of DFT with using 6-311++G(d,p) basis sets. Thanks to geometry optimization calculations, conformations energies were obtained. And stable conformer was detected. And then radicals were modeled by using the conformer that has the lowest energy. Finally, calculated values are compared with experimental data.

Keywords

• Three-carboxyfuran
• Molecular Modelling
• DFT
• Conformational Analysis
• Radical models

References

1. Aras, E., Aşik, B., Eken, M., & Birey, M. (2006). EPR study of γ-irradiated three-furancarboxylic acid. Radiation Effects & Defects in Solids, 161(6), 373-376.
2. Chipman, D. M. (1994). Magnetic Hyperfine Coupling Constants in Free Radicals. In Quantum mechanical electronic structure calculations with chemical accuracy. Kluwer Academic Publishers.
3. Dereli, Ö., Erdoğdu, Y., Ateş, L., Sarıkaya, E. K., & Özturan, F. P. (2017). Molecule and Radical Structures of Isobutyronitrile. Gazi University Journal of Science, 30(1), 161-165.
4. Derelı, Ö., Sarikaya, E. K., & Erdoğdu, Y. (2018). Investigation of molecular and radical structures of ethylene glycol. AIP Conference Proceedings,
5. Frisch, M. J., & al., e. t. (2003). Gaussian 03. In Gaussian, Inc. http://www.gaussian.com/g_misc/g03/citation_g03.htm
6. Irvine. (2008). Spartan 08 (Spartan Molecular Database) Wavefunction Inc., CA 92612 USA.
7. Kurth, S., Marques, M., & Gross, E. (2005). Density-functional theory. Elsevier Ltd.
8. Neese, F. (2001). Prediction of electron paramagnetic resonance g values using coupled perturbed Hartree-Fock and Kohn-Sham theory. Journal of Chemical Physics, 115(24), 11080-11096. https://doi.org/Doi 10.1063/1.1419058

9. Sarıkaya, E. K., Bahçeli, S., Varkal, D., & Dereli, Ö. (2017). FT-IR, micro-Raman and UV–vis spectroscopic and quantum chemical calculation studies on the 6-chloro-4-hydroxy-3-phenyl pyridazine compound. Journal of Molecular Structure, 1141, 44-52.
10. Sarikaya, E. K., & Dereli, O. (2014). Study on molecular structure and vibrational spectra of 5,7-dimethoxycoumarin using DFT: A combined experimental and quantum chemical approach. Optics and Spectroscopy, 117(2), 240-249. https://doi.org/10.1134/S0030400x14070108
11. Sarikaya, E. K., Dereli, O., Erdogdu, Y., & Gulluoglu, M. T. (2013). Molecular structure and vibrational spectra of 7-Ethoxycoumarin by density functional method. Journal of Molecular Structure, 1049, 220-226. https://doi.org/10.1016/j.molstruc.2013.06.026
12. Sarikaya, E. K., & Dereli, Ö. (2017). Theoretical calculations of Electron Paramagnetic Resonance parameters of liquid phase Orotic acid radical [AIP Conference Proceedings]. AIP Conference Proceedings, 1815(1), 030005.
13. Sarikaya, E. K., & Dereli, Ö. (2017). Theoretical calculations of EPR parameters of gas phase hydracrylonitrile radical. AIP Conference Proceedings, 1815(1), 030006.
14. Sarıkaya, E. K., & Dereli, Ö. (2013). Molecular structure and vibrational spectra of 7-Methoxy-4-methylcoumarin by density functional method. Journal of Molecular Structure, 1052, 214-220.
15. Sarıkaya, E. K., Dereli, Ö., Erdoğdu, Y., & Güllüoğlu, M. (2013). Molecular structure and vibrational spectra of 7-Ethoxycoumarin by density functional method. Journal of Molecular Structure, 1049, 220-226.
16. Sarikaya, E. K., Erdoğdu, Y., & Derelı, Ö. (2018). Determination of EPR parameters of gamma-irradiated powder limettin sample by experimental and theoretical studies [AIP Conference Proceedings]. AIP Publishing, 2042(1), 020019. https://doi.org/10.1063/1.5078891
17. Schuchardt, K. L., Didier, B. T., Elsethagen, T., Sun, L., Gurumoorthi, V., Chase, J., Li, J., & Windus, T. L. (2007). Basis set exchange: a community database for computational sciences. Journal of chemical information and modeling, 47(3), 1045-1052.