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Original scientific paper
https://doi.org/10.5562/cca3026

Structural and Antioxidative Features of Chlorogenic Acid

Jelena Tošović   ORCID icon orcid.org/0000-0001-5531-7193 ; University of Kragujevac, Faculty of Science, Radoja Domanovića 12, 34000 Kragujevac, Serbia
Svetlana Marković   ORCID icon orcid.org/0000-0003-3483-3599 ; University of Kragujevac, Faculty of Science, Radoja Domanovića 12, 34000 Kragujevac, Serbia

Fulltext: english, pdf (1 MB) pages 535-541 downloads: 1.247* cite
APA 6th Edition
Tošović, J. & Marković, S. (2016). Structural and Antioxidative Features of Chlorogenic Acid. Croatica Chemica Acta, 89 (4), 535-541. https://doi.org/10.5562/cca3026
MLA 8th Edition
Tošović, Jelena and Svetlana Marković. "Structural and Antioxidative Features of Chlorogenic Acid." Croatica Chemica Acta, vol. 89, no. 4, 2016, pp. 535-541. https://doi.org/10.5562/cca3026. Accessed 20 Oct. 2021.
Chicago 17th Edition
Tošović, Jelena and Svetlana Marković. "Structural and Antioxidative Features of Chlorogenic Acid." Croatica Chemica Acta 89, no. 4 (2016): 535-541. https://doi.org/10.5562/cca3026
Harvard
Tošović, J., and Marković, S. (2016). 'Structural and Antioxidative Features of Chlorogenic Acid', Croatica Chemica Acta, 89(4), pp. 535-541. https://doi.org/10.5562/cca3026
Vancouver
Tošović J, Marković S. Structural and Antioxidative Features of Chlorogenic Acid. Croatica Chemica Acta [Internet]. 2016 [cited 2021 October 20];89(4):535-541. https://doi.org/10.5562/cca3026
IEEE
J. Tošović and S. Marković, "Structural and Antioxidative Features of Chlorogenic Acid", Croatica Chemica Acta, vol.89, no. 4, pp. 535-541, 2016. [Online]. https://doi.org/10.5562/cca3026

Abstracts
This work contributes to the structure clarification of chlorogenic acid (5-O-caffeoylquinic acid, 5CQA) by comparing the experimental and simulated IR, Raman, 1H-NMR, 13C-NMR, and UV-vis spectra. The lowest-energy conformers in the gas-phase and solution were used for all calculations. Very good agreement between all experimental and simulated spectra indicates correct arrangement of the atoms in the 5CQA molecule. In addition, the bond dissociation enthalpies, proton affinities, electron transfer enthalpies, ionization potentials, and proton dissociation enthalpies for 5CQA were used for thermodynamic consideration of the major antioxidative mechanisms: HAT (Hydrogen Atom Transfer), SPLET (Sequential Proton-Loss Electron-Transfer), and SET-PT (Single Electron Transfer – Proton Transfer). It was found that HAT may be the predominant mechanism in nonpolar solvents, while HAT and SPLET are competitive pathways in polar media.
All quantum-chemical calculations were carried out by means of the MN12-SX method. Its performance is similar to those of the B3LYP-D2, B3LYP-D3, and M06-2X functionals.

Creative Commons License This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords
chlorogenic acid; spectral properties; thermodynamic parameters; MN12-SX

Hrčak ID: 179369

URI
https://hrcak.srce.hr/179369

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