The pH-dependence of organofluorine binding domain preference in dissolved humic acid

Chemosphere

Volumn 90, Issue 2, 2013, Pages 270-275

  Longstaffe, James G ^a   Courtier Murias, Denis ^a   Simpson, André J ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Environmental interactions; Humic acid; Nuclear Magnetic Resonance; Organofluorine; Saturation Transfer Difference

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; BINDING ENERGY; BIOCHEMISTRY; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS;

CONFORMATIONAL CHANGE; ENVIRONMENTAL INTERACTIONS; HUMIC ACID; INTRA-MOLECULAR HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE(NMR); ORGANOFLUORINE; SATURATION-TRANSFER DIFFERENCES; SPECIFIC INTERACTION;

NUCLEAR MAGNETIC RESONANCE;

HEXAFLUOROBENZENE; HUMIC ACID; ORGANOFLUORINE DERIVATIVE; PENTAFLUOROANILINE; PENTAFLUOROPHENOL; UNCLASSIFIED DRUG;

CARBOHYDRATE; CHEMICAL BINDING; CHEMICAL COMPOSITION; DISSOLVED MATTER; HUMIC ACID; HYDROPHOBICITY; NUCLEAR MAGNETIC RESONANCE; ORGANOFLUORINE; PH; SATURATION; XENOBIOTICS;

ARTICLE; BINDING SITE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; ELECTRON TRANSPORT; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH;

EID: 84869878515     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2012.07.004     Document Type: Article

References (35)

1. Boys S.F., Bernardi R. The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Mol. Phys. 1970, 19:553-566.
2. Chefetz B., Xing B. Relative role of aliphatic and aromatic moieties as sorption domains for organic compounds: a review. Environ. Sci. Technol. 2009, 43:1680-1688.
3. Chefetz B., Deshmukh A.P., Hatcher P.G. Pyrene sorption by natural organic matter. Environ. Sci. Technol. 2000, 34:2925-2930.
4. Chin Y.-P., Aiken G.R., Danielsen K.M. Binding of pyrene to aquatic and commercial humic substances: the role of molecular weight and aromaticity. Environ. Sci. Technol. 1997, 31:1630-1635.
5. Chiou C.T., Malcom R.L., Brinton T.I., Kile D.E. Water solubility enhancement of some organic pollutants and pesticides by dissolved humic and fulvic acids. Environ. Sci. Technol. 1986, 20:502-508.
6. Garbarini D.R., Lion L.W. Influence of the nature of soil organics on the sorption of toluene and trichloroethylene. Environ. Sci. Technol. 1986, 20:1263-1269.
7. Golding C.J., Smernik R.J., Birch G.F. Investigation of the role of structural domains identified in sedimentary organic matter in the sorption of hydrophobic organic compounds. Environ. Sci. Technol. 2005, 39:3925-3932.
8. Gunasekara A.S., Simpson M.J., Xing B. Identification and characterization of sorption domains in soil organic matter using structurally modified humic acids. Environ. Sci. Technol. 2003, 37:852-858.
9. 5X stacking interactions. J. Org. Chem. 2006, 71:9261-9270.
10. Karickhoff S.W., Morris K.R. Sorption dynamics of hydrophobic pollutants in sediment suspensions. Environ. Toxicol. Chem. 1985, 4:469-479.
11. Karickhoff S.W., Brown D.S., Scott T.A. Sorption of hydrophobic pollutants on natural sediments. Water Res. 1979, 13:241-248.
12. Kelleher B.P., Simpson A.J. Humic substances in soils: are they really chemically distinct?. Environ. Sci. Technol. 2006, 40:4605-4611.
13. 19F NMR investigation of hexafluorobenzene sorption to soil organic matter. Environ. Sci. Technol. 2000, 34:204-210.
14. 2O. J. Inorg. Biochem. 2004, 98:161-166.
15. 1H heteronuclear saturation transfer difference nuclear magnetic resonance spectroscopy. Environ. Toxicol. Chem. 2011, 30:1745-1753.
16. 19F} reverse heteronuclear saturation transfer difference NMR spectroscopy. Environ. Sci. Technol. 2010, 44:5476-5482.
17. 13C correlation solid-state nuclear magnetic resonance. Environ. Sci. Technol. 2001, 35:1928-1934.
18. Mao J.-D., Tremblay L., Gagné J.-P., Kohl S., Rice J., Schmidt-Rohr K. Humic acids from particulate organic matter in the Saguenay Fjord and the St. Lawrence Estuary investigated by advanced solid-state NMR. Geochim. Cosmochim. Acta 2007, 71:5483-5499.
19. Pan B., Ghosh S., Xing B. Nonideal binding between dissolved humic acids and polyaromatic hydrocarbons. Environ. Sci. Technol. 2007, 41:6472-6478.
20. Pan B., Ghosh S., Xing B. Dissolved organic matter conformation and its interaction with pyrene as affected by water chemistry and concentration. Environ. Sci. Technol. 2008, 42:1594-1599.
21. Piccolo A., Conte P., Spaccini R., Chiarella M. Effects of some dicarboxylic acids on the association of dissolved humic substances. Biol. Fertil. Soils 2003, 37:255-259.
22. Robertson B.K., Alexander M. Sequestration of DDT and dieldrin in soil: disappearance of acute toxicity but not the compounds. Environ. Toxicol. Chem. 1998, 17:1034-1038.
23. Schmidt M.W., Baldridge K.K., Boatz J.A., Elbert S.T., Gordon M.S., Jensen J.H., Koseki J.A., Matsunaga N., Nguyen K.A., Su S.J., Windus T.L., Dupuis M., Montgomery J.A. General atomic and molecular electronic structure system. J. Comput. Chem. 1993, 14:1347-1363.
24. Simpson A.J., Kingery W.L., Spraul M., Humpfer E., Dvortsak P., Kerssebaum R. Separation of structural components in soil organic matter by diffusion ordered spectroscopy. Environ. Sci. Technol. 2001, 35:4421-4425.
25. Simpson A.J., Simpson M.J., Smith E., Kelleher B.P. Microbially derived inputs to soil organic matter: are current estimates too low?. Environ. Sci. Technol. 2007, 41:8070-8076.
26. Sinnokrot M.O., Sherrill C.D. Substituent effects in π-π interactions: sandwich and T-shaped configurations. J. Am. Chem. Soc. 2004, 126:7690-7697.
27. Smejkalová D., Piccolo A. Aggregation and disaggregation of humic supramolecular assemblies by NMR diffusion ordered spectroscopy (DOSY-NMR). Environ. Sci. Technol. 2008, 42:699-706.
28. Smejkalová D., Spaccini R., Fontaine B., Piccolo A. Binding of phenol and differently halogenated phenols to dissolved humic matter as measured by NMR spectroscopy. Environ. Sci. Technol. 2009, 43:5377-5382.
29. Sun H., Zhu D., Mao J. Sorption of polar and nonpolar aromatic compounds to two humic acids with varied structural heterogeneity. Environ. Toxicol. Chem. 2008, 27:2449-2456.
30. Wang X., Cook R., Tao S., Xing B. Sorption of organic contaminants by biopolymers: role of polarity, structure and domain spatial arrangement. Chemosphere 2007, 66:1476-1484.
31. Wu D., Chen A., Johnson C.S. An improved diffusion-ordered spectroscopy experiment incorporating bipolar-gradient pulses. J. Magn. Reson., Ser. A 1995, 115:260-264.
32. Xing B., Pignatello J.J. Dual-mode sorption of low-polarity compounds in glassy poly(vinyl chloride) and soil organic matter. Environ. Sci. Technol. 1997, 31:792-799.
33. Xing B., McGill W.B., Dudas M.J. Sorption of α-naphthol onto organic sorbents varying in polarity and aromaticity. Chemosphere 1994, 28:145-153.
34. Xing B., Pignatello J.J., Gigliotti B. Competitive sorption between atrazine and other organic compounds in soils and model sorbents. Environ. Sci. Technol. 1996, 30:2432-2440.
35. Zhu D., Hyun S., Pignatello J.J., Lee L.S. Evidence for π-π electron donor-acceptor interactions between π-donor aromatic compounds and π-acceptor sites in soil organic matter through pH effects on sorption. Environ. Sci. Technol. 2004, 38:4361-4368.