Issue

Vol. 33 No. 4 (2021): Vol 33 Issue 4

Copyright (c) 2021 AJC

Creative Commons License

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

Free Radical Scavenging Activity of Dihydrocaffeic Acid: A Quantum Chemical Approach

https://doi.org/10.14233/ajchem.2021.23068
K. Senthilkumar
Department of Physics, Government Arts College, Udumalpet, Tirupur-642126, India
S.S. Naina Mohammed
Department of Physics, Government Arts College, Udumalpet, Tirupur-642126, India
S. Kalaiselvan
Department of Chemistry, M. Kumarasamy College of Engineering, Karur-639113, India

Corresponding Author(s) : S. Kalaiselvan

kalaichem82@gmail.com

Asian Journal of Chemistry, Vol. 33 No. 4 (2021): Vol 33 Issue 4

Abstract

Based on density functional theory (DFT), to investigate relationships between the antioxidant activity and structure of dihydrocaffeic acid, quantum chemical calculation is used. The optimized structures of the neutral, radical and ionic forms have been carried out by DFT-B3LYP method with the 6-311G(d,p) basis set. Reaction enthalpies related with the hydrogen atom transfer (HAT), single electron transfer proton transfer (SET-PT) and sequential proton loss and electron transfer (SPLET) were calculated in gas and water phase. The HOMO-LUMO energy gap, electron affinity, electronegativity, ionization energy, hardness, chemical potential, global softness and global electrophilicity were calculated by using the same level of theory. Surfaces with a molecular electrostatic potential (MEP) were studied to determine the reactive sites of dihydrocaffeic acid. The difference in energy between the donor and acceptor as well as the stabilization energy was determined through the natural bond orbital (NBO) analysis. The Fukui index (FI) based on electron density was employed to predict reaction sites. Reaction enthalpies are compared with previously published data for phenol and 3,4-dihydroxycinnamic acid.

Keywords

Density functional theory Dihydrocaffeic acid Fukui index
Senthilkumar, K., Naina Mohammed, S., & Kalaiselvan, S. (2021). Free Radical Scavenging Activity of Dihydrocaffeic Acid: A Quantum Chemical Approach. Asian Journal of Chemistry, 33(4), 937–944. https://doi.org/10.14233/ajchem.2021.23068
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. X. Zhou, M. Zhou, Y. Liu, Q. Ye, J. Gu and G. Luo, Int. J. Food Prop., 19, 233 (2016); https://doi.org/10.1080/10942912.2014.983607
  2. B.M. Fraga, A. González-Coloma, S. Alegre-Gómez, M. LópezRodríguez, L.J. Amador and C.E. Díaz, Phytochemistry, 133, 59 (2017); https://doi.org/10.1016/j.phytochem.2016.10.008
  3. W.S. Feng, B. Zhu, X.K. Zheng, Y.L. Zhang, L.G. Yang and Y.J. Li, Chin. J. Nat. Med., 9, 108 (2011).
  4. D.S. Goldstein, R. Stull, S.P. Markey, E.S. Marks and H.R. Keiser, J. Chromatogr. B, 311, 148 (1984); https://doi.org/10.1016/S0378-4347(00)84701-5
  5. W.A. Pryor, Free Radic. Biol. Med., 28, 141 (2000); https://doi.org/10.1016/S0891-5849(99)00224-5
  6. M. Hahn, M. Baierle, M.F. Charão, G.B. Bubols, F.S. Gravina, P. Zielinsky, M.D. Arbo and S. Cristina Garcia, Drug Chem. Toxicol., 40, 368 (2017); https://doi.org/10.1080/01480545.2016.1212365
  7. M. Dizdaroglu, P. Jaruga, M. Birincioglu and H. Rodriguez, Free Radic. Biol. Med., 32, 1102 (2002); https://doi.org/10.1016/S0891-5849(02)00826-2
  8. A.C. Maritim, R.A. Sanders and J.B. Watkins, J. Biochem. Mol. Toxicol., 17, 24 (2003); https://doi.org/10.1002/jbt.10058
  9. A.J. Javan, M.J. Javan and Z.A. Tehrani, J. Agric. Food Chem., 61,1534 (2013); https://doi.org/10.1021/jf304926m
  10. Y. Xue, Y. Zheng, L. An, Y. Dou and Y. Liu, Food Chem., 151, 198 (2014); https://doi.org/10.1016/j.foodchem.2013.11.064
  11. G. Mazzone, N. Malaj, N. Russo and M. Toscano, Food Chem., 141, 2017 (2013); https://doi.org/10.1016/j.foodchem.2013.05.071
  12. N. Nenadis, H.Y. Zhang and M.Z. Tsimidou, J. Agric. Food Chem., 51, 1874 (2003); https://doi.org/10.1021/jf0261452
  13. J. Lengyel, J. Rimarcik, A. Vaganek and E. Klein, Phys. Chem. Chem. Phys., 15, 10895 (2013); https://doi.org/10.1039/c3cp00095h
  14. J.S. Wright, E.R. Johnson and G.A. DiLabio, J. Am. Chem. Soc., 123, 1173 (2001); https://doi.org/10.1021/ja002455u
  15. D.A. Pratt, G.A. DiLabio, G. Brigati, G.F. Pedulli and L. Valgimigli, J. Am. Chem. Soc., 123, 4625 (2001); https://doi.org/10.1021/ja005679l
  16. M. Wijtmans, D.A. Pratt, L. Valgimigli, G.A. DiLabio, G.F. Pedulli and N.A. Porter, Angew. Chem. Int. Ed., 42, 4370 (2003); https://doi.org/10.1002/anie.200351881
  17. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, J.J. Heyd, M. Bearpark, J.E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Ross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski and D.J. Fox, Gaussian 09, Revision D.01; Gaussian Wallingford, CT (2009).
  18. A. Becke, J. Chem. Phys., 98, 5648 (1993); https://doi.org/10.1063/1.464913
  19. C. Lee, W. Yang and R.G. Parr, Phys. Rev. B Condens. Matter, 37, 785 (1988); https://doi.org/10.1103/PhysRevB.37.785
  20. E.D. Glendening, J.K. Badenhoop, A.E. Reed, J.E. Carpenter, J.A. Bohmann and C.M. Morales, Weinhold F. NBO 3.1 Theoretical Chemistry Institute and Department of Chemistry, University of Wisconsin, Madison, USA (2001).
  21. J. Tomasi and M. Persico, Chem. Rev., 94, 2027 (1994); https://doi.org/10.1021/cr00031a013
  22. V. Barone, M. Cossi and J.A. Tomasi, J. Chem. Phys., 107, 3210 (1997); https://doi.org/10.1063/1.474671
  23. P. Geerlings, F. De Proft and W. Langenaeker, Chem. Rev., 103, 1793 (2003); https://doi.org/10.1021/cr990029p
  24. T. Okada, M. Yamakawa, N. Ohmori, S. Mori, H. Horikawa, T. Hayashi and S. Fujishima, Chem. Cent. J., 4, 1 (2010); https://doi.org/10.1186/1752-153X-4-1
  25. J.L. Gazquez, A. Cedillo and A. Vela, J. Phys. Chem. A, 111, 1966 (2007); https://doi.org/10.1021/jp065459f
  26. M. Leopoldini, T. Marino, N. Russo and M. Toscano, J. Phys. Chem. A, 108, 4916 (2004); https://doi.org/10.1021/jp037247d
  27. K. Sadasivam and R. Kumaresan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 79, 282 (2011); https://doi.org/10.1016/j.saa.2011.02.042
  28. M. Lucarini, P. Pedrielli, G.F. Pedulli, S. Cabiddu and C. Fattuoni, J. Org. Chem., 61, 9259 (1996); https://doi.org/10.1021/jo961039i
  29. R.A. Jackson and K.M. Hosseini, J. Chem. Soc. Chem. Commun., 13, 967 (1992); https://doi.org/10.1039/C39920000967
  30. D.D.M. Wayner, E. Lusztyk, K.U. Ingold and P. Mulder, J. Org. Chem., 61, 6430 (1996); https://doi.org/10.1021/jo952167u
  31. E. Klein and V. Lukes, J. Phys. Chem. A, 110, 12312 (2006); https://doi.org/10.1021/jp063468i
  32. M. Nsangou, J.J. Fifen, Z. Dhaouadi and S. Lahmar, J. Mol. Struct. THEOCHEM, 862, 53 (2008); https://doi.org/10.1016/j.theochem.2008.04.028
  33. F. Martorana, M. Foti, A. Virtuoso, D. Gaglio, F. Aprea, T. Latronico, R. Rossano, P. Riccio, M. Papa, L. Alberghina and A.M. Colangelo, Oxid. Med. Cell. Longev., 2019, 1 (2019); https://doi.org/10.1155/2019/8056904
  34. F.A.M. Silva, F. Borges, C. Guimaraes, J.L.F.C. Lima, C. Matos and S. Reis, J. Agric. Food Chem., 48, 2122 (2000); https://doi.org/10.1021/jf9913110
  35. J.P. Tomasi and P.D. Truhlar, Chemical Application of Atomic and Molecular Electrostatic Potentials, Plenum: New York (1981).
  36. M.N. Arshad, A.M. Asiri, K.A. Alamry, T. Mahmood, M.A. Gilani, K. Ayub and A.S. Birinji, Spectrochim. Acta A Mol. Biomol. Spectrosc., 142, 364 (2015); https://doi.org/10.1016/j.saa.2015.01.101
  37. K. Fukui, T. Yonezawa and H. Shingu, J. Chem. Phys., 20, 722 (1952); https://doi.org/10.1063/1.1700523
  38. K.O. Sulaiman and A.T. Onawole, Comput. Theor. Chem., 1093, 73 (2016); https://doi.org/10.1016/j.comptc.2016.08.014
  39. C.J. Parkinson, P.M. Mayer and L. Radom, J. Chem. Soc., Perkin Trans. 2, 11, 2305 (1999); https://doi.org/10.1039/a905476f
  40. F. Weinhold and C.R. Landis, Chem. Educ. Res. Pract., 2, 91 (2001); https://doi.org/10.1039/B1RP90011K
  41. M. Szafran, A. Komasa and E. Bartoszak-Adamska, J. Mol. Struct. THEOCHEM, 827, 101 (2007); https://doi.org/10.1016/j.molstruc.2006.05.012
  42. Y. Erdogdu, O. Unsalan, M. Amalanathan and I. Hubert Joe, J. Mol. Struct., 980, 24 (2010); https://doi.org/10.1016/j.molstruc.2010.06.032
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0