Table of Contents
International Journal of Chemical Physics
Volume 2015 (2015), Article ID 835707, 13 pages
http://dx.doi.org/10.1155/2015/835707
Research Article

Proton-Coupled Electron Transfer in the Reaction of 3,4-Dihydroxyphenylpyruvic Acid with Reactive Species in Various Media

1Department of Physics, Faculty of Science, The University of Ngaoundere, P.O. Box 454, Ngaoundere, Cameroon
2Laboratoire de Spectroscopie Atomique, Moléculaire et Applications, Faculté des Sciences de Tunis, Université de Tunis El Manar, Campus Universitaire, 1060 Tunis, Tunisia
3University of Maroua, P.O. Box, 46 Maroua, Cameroon
4Fundamental Physics Lab, Graduate Training Unit in Physics and Engineering Sciences, Faculty of Science, University of Douala, P.O. Box 24157, Douala, Cameroon

Received 26 August 2014; Revised 21 December 2014; Accepted 22 December 2014

Academic Editor: Franck Rabilloud

Copyright © 2015 J. J. Fifen et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. I. Cukier and D. G. Nocera, “Proton-coupled electron transfer,” Annual Review of Physical Chemistry, vol. 49, no. 1, pp. 337–369, 1998. View at Publisher · View at Google Scholar · View at Scopus
  2. M. H. V. Huynh and T. J. Meyer, “Proton-coupled electron transfer,” Chemical Reviews, vol. 107, no. 11, pp. 5004–5064, 2007. View at Publisher · View at Google Scholar · View at Scopus
  3. J. J. Fifen, M. Nsangou, Z. Dhaouadi, O. Motapon, and N. Jaidane, “Solvent effects on the antioxidant activity of 3,4-dihydroxyphenylpyruvic acid: DFT and TD-DFT studies,” Computational and Theoretical Chemistry, vol. 966, no. 1–3, pp. 232–243, 2011. View at Publisher · View at Google Scholar · View at Scopus
  4. K. Senthil kumar and R. Kumaresan, “A DFT Study on the structural, electronic properties and radical scavenging mechanisms of calycosin, glycitein, pratensein and prunetin,” Computational and Theoretical Chemistry, vol. 985, pp. 14–22, 2012. View at Publisher · View at Google Scholar · View at Scopus
  5. M. Najafi, M. Zahedi, and E. Klein, “DFT/B3LYP study of the solvent effect on the reaction enthalpies of homolytic and heterolytic O—H bond cleavage in mono-substituted chromans,” Computational and Theoretical Chemistry, vol. 978, no. 1–3, pp. 16–28, 2011. View at Publisher · View at Google Scholar · View at Scopus
  6. M. Najafi, K. H. Mood, M. Zahedi, and E. Klein, “DFT/B3LYP study of the substituent effect on the reaction enthalpies of the individual steps of single electron transfer-proton transfer and sequential proton loss electron transfer mechanisms of chroman derivatives antioxidant action,” Computational and Theoretical Chemistry, vol. 969, no. 1–3, pp. 1–12, 2011. View at Publisher · View at Google Scholar · View at Scopus
  7. K. Sadasivam and R. Kumaresan, “Theoretical investigation on the antioxidant behavior of chrysoeriol and hispidulin flavonoid compounds—a DFT study,” Computational and Theoretical Chemistry, vol. 963, no. 1, pp. 227–235, 2011. View at Publisher · View at Google Scholar · View at Scopus
  8. D. Mikulski, M. Szelaogonekg, M. Molski, and R. Górniak, “Quantum-chemical study on the antioxidation mechanisms of trans-resveratrol reactions with free radicals in the gas phase, water and ethanol environment,” Journal of Molecular Structure: THEOCHEM, vol. 951, no. 1–3, pp. 37–48, 2010. View at Publisher · View at Google Scholar · View at Scopus
  9. J. Rimarčík, V. Lukeš, E. Klein, and M. Ilčin, “Study of the solvent effect on the enthalpies of homolytic and heterolytic N–H bond cleavage in p-phenylenediamine and tetracyano-p-phenylenediamine,” Journal of Molecular Structure, vol. 952, no. 1–3, pp. 25–30, 2010. View at Publisher · View at Google Scholar · View at Scopus
  10. J. H. Fellman, T. S. Fujita, and E. S. Roth, “Substrate specificity of p-hydroxyphenylpyruvate hydroxylase,” Biochimica et Biophysica Acta, vol. 268, no. 2, pp. 601–604, 1972. View at Google Scholar · View at Scopus
  11. S. Lindstedt and M. Rundgren, “Blue color, metal content, and substrate binding in 4-hydroxyphenylpyruvate dioxygenase from Pseudomonas sp. strain P.J. 874,” The Journal of Biological Chemistry, vol. 257, no. 20, pp. 11922–11931, 1982. View at Google Scholar · View at Scopus
  12. M. Nsangou, J. J. Fifen, Z. Dhaouadi, and S. Lahmar, “Hydrogen atom transfer in the reaction of hydroxycinnamic acids with radical · OH and radical · HO2 radicals: DFT study,” Journal of Molecular Structure, vol. 862, no. 1–3, pp. 53–59, 2008. View at Publisher · View at Google Scholar · View at Scopus
  13. M. R. Alberto, M. E. Farías, and M. C. M. de Nadra, “Effect of gallic acid and catechin on Lactobacillus hilgardii 5w growth and metabolism of organic compounds,” Journal of Agricultural and Food Chemistry, vol. 49, no. 9, pp. 4359–4363, 2001. View at Publisher · View at Google Scholar · View at Scopus
  14. M. R. Alberto, M. E. Farías, and M. C. Manca de Nadra, “Effect of wine phenolic compounds on Lactobacillus hilgardii 5w viability,” Journal of Food Protection, vol. 65, no. 1, pp. 211–213, 2002. View at Google Scholar · View at Scopus
  15. M. Alberto, C. Gomez-Cordoves, and M. M. de Nadra, “Metabolism of gallic acid and catechin by Lactobacillus hilgardii from wine,” Journal of Agricultural and Food Chemistry, vol. 52, no. 21, pp. 6465–6469, 2004. View at Publisher · View at Google Scholar · View at Scopus
  16. M. J. Rodríguez Vaquero, M. R. Alberto, and M. C. Manca de Nadra, “Influence of phenolic compounds from wines on the growth of Listeria monocytogenes,” Food Control, vol. 18, no. 5, pp. 587–593, 2007. View at Publisher · View at Google Scholar · View at Scopus
  17. H. Milane, La quercétine et ses dérivés: molécules à caractère pro-oxydant ou capteurs de radicaux libres; études et applications thérapeutiques [Ph.D. thesis], Université Louis Pasteur-Strasbourg I, 2004.
  18. J. J. Fifen, M. Nsangou, Z. Dhaouadi, O. Motapon, and S. Lahmar, “Single or double hydrogen atom transfer in the reaction of metal—associated phenolic acids with OH radical: DFT Study,” Journal of Molecular Structure: THEOCHEM, vol. 901, no. 1–3, pp. 49–55, 2009. View at Publisher · View at Google Scholar · View at Scopus
  19. D. M. Miller, G. R. Buettner, and S. D. Aust, “Transition metals as catalysts of autoxidation reactions,” Free Radical Biology and Medicine, vol. 8, no. 1, pp. 95–108, 1990. View at Publisher · View at Google Scholar · View at Scopus
  20. E. Cadenas and H. Sies, “The lag phase,” Free Radical Research, vol. 28, no. 6, pp. 601–609, 1998. View at Publisher · View at Google Scholar · View at Scopus
  21. N. Pastor, H. Weinstein, E. Jamison, and M. Brenowitz, “A detailed interpretation of OH radical footprints in a TBP-DNA complex reveals the role of dynamics in mechanism of sequence-specific binding,” Journal of Molecular Biology, vol. 304, no. 1, pp. 55–68, 2000. View at Publisher · View at Google Scholar · View at Scopus
  22. T. N. Truong and D. G. Truhlar, “Ab initio transition state theory calculations of the reaction rate for OH+CH4H2O+CH3,” The Journal of Chemical Physics, vol. 93, no. 3, pp. 1761–1769, 1990. View at Publisher · View at Google Scholar · View at Scopus
  23. R. T. Skodje and D. G. Truhlar, “Parabolic tunneling calculations,” The Journal of Physical Chemistry, vol. 85, no. 6, pp. 624–628, 1981. View at Publisher · View at Google Scholar · View at Scopus
  24. E. Wigner, “Crossing of potential thresholds in chemical reactions,” Zeitschrift für Physikalische Chemie B, vol. 19, pp. 203–216, 1932. View at Google Scholar
  25. D. G. Truhlar and A. Kuppermann, “Exact tunneling calculations,” Journal of the American Chemical Society, vol. 93, no. 8, pp. 1840–1851, 1971. View at Publisher · View at Google Scholar · View at Scopus
  26. D. G. Truhlar and A. Kuppermann, “A test of transition state theory against exact quantum mechanical calculations,” Chemical Physics Letters, vol. 9, no. 3, pp. 269–272, 1971. View at Publisher · View at Google Scholar
  27. C. Eckart, “The penetration of a potential barrier by electrons,” Physical Review, vol. 35, no. 11, pp. 1303–1309, 1930. View at Publisher · View at Google Scholar · View at Scopus
  28. J. Zheng, S. Zhang, B. J. Lynch et al., POLYRATE-version 2010, 2010.
  29. J. Tomasi, B. Mennucci, and R. Cammi, “Quantum mechanical continuum solvation models,” Chemical Reviews, vol. 105, no. 8, pp. 2999–3093, 2005. View at Publisher · View at Google Scholar · View at Scopus
  30. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., Gaussian 03, Gaussian, Inc, Wallingford, Conn, USA, 2004.
  31. A. D. Becke, “Density-functional exchange-energy approximation with correct asymptotic behavior,” Physical Review A, vol. 38, no. 6, pp. 3098–3100, 1988. View at Publisher · View at Google Scholar · View at Scopus
  32. C. Lee, W. Yang, and R. G. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Physical Review B, vol. 37, no. 2, pp. 785–789, 1988. View at Publisher · View at Google Scholar · View at Scopus
  33. V. A. Rassolov, M. A. Ratner, J. A. Pople, P. C. Redfern, and L. A. Curtiss, “631G basis set for thirdrow atoms,” Journal of Computational Chemistry, vol. 22, no. 9, pp. 976–984, 2001. View at Publisher · View at Google Scholar
  34. M. J. Frisch, J. A. Pople, and J. S. Binkley, “Self-consistent molecular orbital methods 25. Supplementary functions for Gaussian basis sets,” The Journal of Chemical Physics, vol. 80, no. 7, pp. 3265–3269, 1984. View at Publisher · View at Google Scholar · View at Scopus
  35. T. Clark, J. Chandrasekhar, G. W. Spitznagel, and P. V. R. Schleyer, “Efficient diffuse function-augmented basis sets for anion calculations. III. The 3-21+G basis set for first-row elements, Li–F,” Journal of Computational Chemistry, vol. 4, no. 3, pp. 294–301, 1983. View at Publisher · View at Google Scholar
  36. A. E. Reed, L. A. Curtiss, and F. Weinhold, “Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint,” Chemical Reviews, vol. 88, no. 6, pp. 899–926, 1988. View at Publisher · View at Google Scholar · View at Scopus
  37. F. Weinhold and J. E. Carpenter, The Structure of Small Molecules and Ions, Plenum, 1988.
  38. L. A. Curtiss, K. Raghavachari, P. C. Redfern, V. Rassolov, and J. A. Pople, “Gaussian-3 (G3) theory for molecules containing first and second-row atoms,” The Journal of Chemical Physics, vol. 109, no. 18, pp. 7764–7776, 1998. View at Publisher · View at Google Scholar · View at Scopus
  39. A. G. Baboul, L. A. Curtiss, P. C. Redfern, and K. Raghavachari, “Gaussian-3 theory using density functional geometries and zero-point energies,” Journal of Chemical Physics, vol. 110, no. 16, pp. 7650–7657, 1999. View at Publisher · View at Google Scholar · View at Scopus
  40. A. Meffert and J. Grotemeyer, “Reactions in molecular clusters: proton transfer to small amino acids,” European Journal of Mass Spectrometry, vol. 1, no. 1, pp. 594–598, 1995. View at Google Scholar
  41. A. Meffert and J. Grotemeyer, “Formation, stability and fragmentation of biomolecular clusters in a superasonic jet investigated with nano- and femtosecond laser pulses,” Physical Chemistry Chemical Physics, vol. 102, no. 3, pp. 459–468, 1998. View at Publisher · View at Google Scholar · View at Scopus
  42. F. H. Yassin and D. S. Marynick, “Computational estimates of the gas-phase acidities of dihydroxybenzoic acid radical cations and their corresponding neutral species,” Journal of Molecular Structure, vol. 629, pp. 223–235, 2003. View at Publisher · View at Google Scholar · View at Scopus
  43. M. Nsangou, Z. Dhaouadi, N. Jaidane, and Z. B. Lakhdar, “DFT study of the structure of hydroxybenzoic acids and their reactions with radical ·OH and ·O2 radicals,” Journal of Molecular Structure: THEOCHEM, vol. 850, no. 1–3, pp. 135–143, 2008. View at Publisher · View at Google Scholar
  44. Z. Dhaouadi, M. Nsangou, N. Garrab, E. H. Anouar, K. Marakchi, and S. Lahmar, “DFT study of the reaction of quercetin with ·O2- and ·OH radicals,” Journal of Molecular Structure, vol. 904, no. 1–3, pp. 35–42, 2009. View at Publisher · View at Google Scholar · View at Scopus
  45. J. E. Bartmess, “Thermodynamics of the electron and the proton,” The Journal of Physical Chemistry, vol. 98, no. 25, pp. 6420–6424, 1994. View at Publisher · View at Google Scholar · View at Scopus
  46. J. J. Fifen, “Thermodynamics of the electron revisited and generalized,” Journal of Chemical Theory and Computation, vol. 9, no. 7, pp. 3165–3169, 2013. View at Publisher · View at Google Scholar · View at Scopus
  47. J. J. Fifen, Z. Dhaouadi, and M. Nsangou, “Revision of the thermodynamics of the proton in gas phase,” The Journal of Physical Chemistry A, vol. 118, no. 46, pp. 11090–11097, 2014. View at Publisher · View at Google Scholar
  48. M. M. Bizarro, B. J. Costa Cabral, R. M. B. Borges dos Santos, and J. A. Martinho Simões, “Substituent effects on the O—H bond dissociation enthalpies in phenolic compounds: agreements and controversies,” Pure and Applied Chemistry, vol. 71, no. 7, pp. 1249–1256, 1999. View at Publisher · View at Google Scholar · View at Scopus
  49. V. D. Parker, “Homolytic bond (H–A) dissociation free energies in solution. Applications of the standard potential of the (H+/H.bul.) couple,” Journal of the American Chemical Society, vol. 114, no. 19, pp. 7458–7462, 1992. View at Publisher · View at Google Scholar · View at Scopus
  50. E. Wilhelm and R. Battino, “Thermodynamic functions of the solubilities of gases in liquids at 25°C,” Chemical Reviews, vol. 73, no. 1, pp. 1–9, 1973. View at Publisher · View at Google Scholar · View at Scopus
  51. M. D. Tissandier, K. A. Cowen, W. Y. Feng et al., “The proton’s absolute aqueous enthalpy and Gibbs free energy of solvation from cluster-ion solvation data,” The Journal of Physical Chemistry A, vol. 102, no. 40, pp. 7787–7794, 1998. View at Publisher · View at Google Scholar · View at Scopus
  52. J. Jortner and R. M. Noyes, “Some thermodynamic properties of the hydrated electron,” Journal of Physical Chemistry, vol. 70, no. 3, pp. 770–774, 1966. View at Publisher · View at Google Scholar · View at Scopus
  53. J. M. Mayer, D. A. Hrovat, J. L. Thomas, and W. T. Borden, “Proton-coupled electron transfer versus hydrogen atom transfer in benzyl/toluene, methoxyl/methanol, and phenoxyl/phenol self-exchange reactions,” Journal of the American Chemical Society, vol. 124, no. 37, pp. 11142–11147, 2002. View at Publisher · View at Google Scholar · View at Scopus
  54. S. Hammes-Schiffer and N. Iordanova, “Theoretical studies of proton-coupled electron transfer reactions,” Biochimica et Biophysica Acta, vol. 1655, no. 1–3, pp. 29–36, 2004. View at Publisher · View at Google Scholar · View at Scopus