Radical sites in humic acids: A theoretical study on protocatechuic and gallic acids

Computational and Theoretical Chemistry

Volumn 1032, Issue , 2014, Pages 42-49

  Šolc, Roland ^a   Gerzabek, Martin H ^a   Lischka, Hans ^b,c   Tunega, Daniel ^a  

^a UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

^b UNIVERSITY OF VIENNA   (Austria)

^c TEXAS TECH UNIVERSITY   (United States)

Author keywords

DFT; EPR; Gallic acid; Humic acids; Protocatechuic acid; Solvation

Indexed keywords

EID: 84894033113     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2014.01.015     Document Type: Article

References (55)

1. Stevenson F.J. Humus Chemistry: Genesis, Composition, Reactions 1994, John Wiley & Sons, New York.
2. Senesi N., Steelink C. Application of ESR spectroscopy to the study of humic substances. Humic Substances II: In Search of Structure 1989, Wiley, New York. M.H.B. Hayes, P. MacCarthy, R.L. Malcolm, R.S. Swift (Eds.).
3. Senesi N. Application of Electron Spin Resonance (ESR) spectroscopy in soil chemistry. Advances in Soil Science 1990, 77-130. Springer, New York. B.A. Stewart (Ed.).
4. Senesi N., Loffredo E. The chemistry of soil organic matter. Soil Physical Chemistry 1999, CRC Press, Boca Raton. second ed. D.L. Sparks (Ed.).
5. Christoforidis K.C., Un S., Deligiannakis Y. High-field 285GHz electron paramagnetic resonance study of indigenous radicals of humic acids. J. Phys. Chem. A 2007, 111:11860-11866.
6. Paul A., Stösser R., Zehl A., Zwirnmann E., Vogt R.D., Steinberg C.E.W. Nature and abundance of organic radicals in natural organic matter: effect of pH and irradiation. Environ. Sci. Technol. 2006, 40:5897-5903.
7. Kummert R., Stumm W. The surface complexation of organic-acids on hydrous gamma-Al2o3. J. Colloid Interface Sci. 1980, 75:373-385.
8. McBride M.B., Wesselink L.G. Chemisorption of catechol on gibbsite, boehmite, and noncrystalline alumina surfaces. Environ. Sci. Technol. 1988, 22:703-708.
9. Boily J.F., Fein J.B. Adsorption of Pb(II) and benzenecarboxylates onto corundum. Chem. Geol. 1998, 148:157-175.
10. Evanko C.R., Dzombak D.A. Influence of structural features on sorption of NOM-analogue organic acids to goethite. Environ. Sci. Technol. 1998, 32:2846-2855.
11. Benyahya L., Garnier J.M. Effect of salicylic acid upon trace-metal sorption (Cd-II, Zn-II, Co-II, and Mn-II) onto alumina, silica, and kaolinite as a function of pH. Environ. Sci. Technol. 1999, 33:1398-1407.
12. Evanko C.R., Dzombak D.A. Surface complexation modeling of organic acid sorption to goethite. J. Colloid Interface Sci. 1999, 214:189-206.
13. Giannakopoulos E., Christoforidis K.C., Tsipis A., Jerzykiewicz M., Deligiannakis Y. Influence of Pb(II) on the radical properties of humic substances and model compounds. J. Phys. Chem. A 2005, 109:2223-2232.
14. 2+ on restricted phyllomorphous clay. Langmuir 2006, 22:6863-6873.
15. Slawinska D., Polewski K., Rolewski P., Slawinski J. Synthesis and properties of model humic substances derived from gallic acid. Int. Agrophys. 2007, 21:199-208.
16. Billes F., Mohammed-Ziegler I., Bombicz P. Vibrational spectroscopic study on the quantum chemical model and the X-ray structure of gallic acid, solvent effect on the structure and spectra. Vib. Spectrosc. 2007, 43:193-202.
17. Mohammed-Ziegler I., Billes F. Vibrational spectroscopic calculations on pyrogallol and gallic acid. J. Mol. Struct.-Theochem. 2002, 618:259-265.
18. Werner I., Bacher A., Eisenreich W. Retrobiosynthetic NMR studies with C-13-labeled glucose - formation of gallic acid in plants and fungi. J. Biol. Chem. 1997, 272:25474-25482.
19. Witwicki M., Jaszewski A.R., Jezierska J., Jerzykiewicz M., Jezierski A. The pH-induced shift in the g-tensor components of semiquinone-type radicals in humic acids - DFT and EPR studies. Chem. Phys. Lett. 2008, 462:300-306.
20. Witwicki M., Jezierska J., Ozarowski A. Solvent effect on EPR, molecular and electronic properties of semiquinone radical derived from 3,4-dihydroxybenzoic acid as model for humic acid transient radicals: high-field EPR and DFT studies. Chem. Phys. Lett. 2009, 473:160-166.
21. Hatzipanayioti D., Petropouleas P. Theoretical and experimental investigation of the semiquinone forms of protocatechuic acid. The effect of manganese. Spectrochim. Acta Part a 2010, 75:997-1007.
22. Witwicki M., Jezierska J. Protonated o-semiquinone radical as a mimetic of the humic acids native radicals: A DFT approach to the molecular structure and EPR properties. Geochim. Cosmochim. Acta 2012, 86:384-391.
23. Fermi E. About the magnetic moments of atomic nuclei. Z. Angew. Phys. 1930, 60:320-333.
24. Kossmann S., Kirchner B., Neese F. Performance of modern density functional theory for the prediction of hyperfine structure: meta-GGA and double hybrid functionals. Mol. Phys. 2007, 105:2049-2071.
25. Improta R., Barone V. Interplay of electronic, environmental, and vibrational effects in determining the hyperfine coupling constants of organic free radicals. Chem. Rev. 2004, 104:1231-1253.
26. Becke A.D. Density-functional thermochemistry.3. The role of exact exchange. J. Chem. Phys. 1993, 98:5648-5652.
27. Lee C.T., Yang W.T., Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density. Phys. Rev. B 1988, 37:785-789.
28. Perdew J.P., Kurth S., Zupan A., Blaha P. Accurate density functional with correct formal properties: a step beyond the generalized gradient approximation. Phys. Rev. Lett. 1999, 82:2544-2547.
29. Neese F., Schwabe T., Grimme S. Analytic derivatives for perturbatively corrected "double hybrid" density functionals: theory, implementation, and applications. J. Chem. Phys. 2007, 126:2049-2071.
30. Beltran J.L., Sanli N., Fonrodona G., Barron D., Ozkan G., Barbosa J. Spectrophotometric, potentiometric and chromatographic pK(a) values of polyphenolic acids in water and acetonitrile-water media. Anal. Chim. Acta 2003, 484:253-264.
31. Schafer A., Horn H., Ahlrichs R. Fully optimized contracted Gaussian-basis sets for atoms Li to Kr. J. Chem. Phys. 1992, 97:2571-2577.
32. Schafer A., Huber C., Ahlrichs R. Fully optimized contracted Gaussian-basis sets of triple zeta valence quality for atoms Li to Kr. J. Chem. Phys. 1994, 100:5829-5835.
33. Amorati R., Pedulli G.F., Guerra M. Hydrogen hyperfine splitting constants for phenoxyl radicals by DFT methods: regression analysis unravels hydrogen bonding effects. Org. Biomol. Chem. 2010, 8:3136-3141.
34. Guerra M., Amorati R., Pedulli G.F. Water effect on the O-H dissociation enthalpy of para-substituted phenols: a DFT study. J. Org. Chem. 2004, 69:5460-5467.
35. Lucarini M., Mugnaini V., Pedulli G.F., Guerra M. Hydrogen-bonding effects on the properties of phenoxyl radicals. An EPR, kinetic, and computational study. J. Am. Chem. Soc. 2003, 125:8318-8329.
36. Tomasi J., Mennucci B., Cances E. The IEF version of the PCM solvation method: an overview of a new method addressed to study molecular solutes at the QM ab initio level. J. Mol. Struct.-Theochem. 1999, 464:211-226.
37. Aquino A.J.A., Tunega D., Haberhauer G., Gerzabek M.H., Lischka H. Acid-base properties of a goethite surface model: a theoretical view. Geochim. Cosmochim. Acta 2008, 72:3587-3602.
38. Aquino A.J.A., Tunega D., Haberhauer G., Gerzabek M.H., Lischka H. Interaction of the 2,4-dichlorophenoxyacetic acid herbicide with soil organic matter moieties: a theoretical study. Eur. J. Soil Sci. 2007, 58:889-899.
39. Barone V. Inclusion of Hartree-Fock exchange in density-functional methods - hyperfine-structure of 2nd row atoms and hydrides. J. Chem. Phys. 1994, 101:6834-6838.
40. Becke A.D. Density-functional exchange-energy approximation with correct asymptotic-behavior. Phys. Rev. A 1988, 38:3098-3100.
41. Perdew J.P. Density-functional approximation for the correlation-energy of the inhomogeneous electron-gas. Phys. Rev. B 1986, 33:8822-8824.
42. Grimme S. Semiempirical GGA-type density functional constructed with a long-range dispersion correction. J. Comput. Chem. 2006, 27:1787-1799.
43. Zhao Y., Truhlar D.G. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theoret. Chem. Acc. 2008, 120:215-241.
44. Tao J.M., Perdew J.P., Staroverov V.N., Scuseria G.E. Climbing the density functional ladder: nonempirical meta-generalized gradient approximation designed for molecules and solids. Phys. Rev. Lett. 2003, 91:146401.
45. Staroverov V.N., Scuseria G.E., Tao J.M., Perdew J.P. Comparative assessment of a new nonempirical density functional: molecules and hydrogen-bonded complexes. J. Chem. Phys. 2003, 119:12129-12137.
46. Grimme S. Semiempirical hybrid density functional with perturbative second-order correlation. J. Chem. Phys. 2006, 124:034108.
47. Sinnecker S., Rajendran A., Klamt A., Diedenhofen M., Neese F. Calculation of solvent shifts on electronic g-tensors with the conductor-like screening model (COSMO) and its self-consistent generalization to real solvents (Direct COSMO-RS). J. Phys. Chem. A 2006, 110:2235-2245.
48. 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, T.M. Ishida, Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.J.A. Montgomery, J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, 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. Cross, 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, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Gaussian Inc., Wallingford CT, 2009.
49. Aquino A.J.A., Tunega D., Haberhauer G., Gerzabek M.H., Lischka H. Solvent effects on hydrogen bonds - a theoretical study. J. Phys. Chem. A 2002, 106:1862-1871.
50. Benisvy L., Bittl R., Bothe E., Garner C.D., McMaster J., Ross S., Teutloff C., Neese F. Phenoxyl radicals hydrogen-bonded to imidazolium: analogues of tyrosyl D of photosystem II: high-field EPR and DFT studies. Angew. Chem.-Int. Ed. 2005, 44:5314-5317.
51. Kaupp M., Gress T., Reviakine R., Malkina O.L., Malkin V.G. G tensor and spin density of the modified tyrosyl radical in galactose oxidase: a density functional study. J. Phys. Chem. B 2003, 107:331-337.
52. Chipman D.M. Hydrogen-bonding effects on free-radical properties. J. Phys. Chem. A 2000, 104:11816-11821.
53. Engstrom M., Himo F., Graslund A., Minaev B., Vahtras O., Agren H. Hydrogen bonding to tyrosyl radical analyzed by ab initio g-tensor calculations. J. Phys. Chem. A 2000, 104:5149-5153.
54. Severino J.F., Goodman B.A., Kay C.W.M., Stolze K., Tunega D., Reichenauer T.G., Pirker K.F. Free radicals generated during oxidation of green tea polyphenols: electron paramagnetic resonance spectroscopy combined with density functional theory calculations. Free Radical Biol. Med. 2009, 46:1076-1088.
55. Eslami A.C., Pasanphan W., Wagner B.A., Buettner G.R. Free radicals produced by the oxidation of gallic acid: an electron paramagnetic resonance study. Chem. Cent. J. 2010, 4:15.