Noncovalent interactions between aromatic compounds and dissolved humic acid examined by nuclear magnetic resonance spectroscopy

Environmental Toxicology and Chemistry

Volumn 23, Issue 2, 2004, Pages 355-362

  Simpson, Myrna J ^a,b   Simpson, André J ^a,b   Hatcher, Patrick G ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

13C Nuclear magnetic resonance; 1H Nuclear magnetic resonance; Contaminant interactions; Humic substances; Spin lattice relaxation

Indexed keywords

AMINO ACIDS; ASSOCIATION REACTIONS; CARBOHYDRATES; ENVIRONMENTAL PROTECTION; IMPURITIES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

HUMIC MATERIALS; NONCOVALENT INTERACTIONS;

AROMATIC COMPOUNDS;

1 NAPHTHOL; ALIPHATIC COMPOUND; AMINO ACID DERIVATIVE; AROMATIC COMPOUND; CARBOHYDRATE; CARBON; CARBON 13; HUMIC ACID; LIGNIN; NAPHTHALENE; PARAFFIN; QUINOLINE;

HUMIC ACID; NUCLEAR MAGNETIC RESONANCE;

ADDITION REACTION; AQUATIC ENVIRONMENT; ARTICLE; BINDING SITE; CHEMICAL COMPOSITION; CHEMICAL INTERACTION; CONCENTRATION RESPONSE; COVALENT BOND; EVALUATION; LAND BIOME; LIQUID; MATHEMATICAL ANALYSIS; MOLECULAR INTERACTION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLLUTION MONITORING; POLLUTION TRANSPORT; PREVALENCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; RELAXATION TIME; SIGNAL DETECTION; SOLID STATE; SUBSTITUTION REACTION;

CARBON ISOTOPES; ENVIRONMENTAL POLLUTANTS; HUMIC SUBSTANCES; HYDROCARBONS, AROMATIC; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY;

EID: 1642579656     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/03-217     Document Type: Article

References (40)

1. Landrum PF, Nihard SR, Eadie BJ, Gardner WS. 1984. Reverse-phase separation method for determining pollutant binding to Aldrich humic acid and dissolved organic carbon of natural waters. Environ Sci Technol 18:187-192.
2. McCarthy JF, Jimenez BD. 1985. Interactions between polycyclic aromatic hydrocarbons and dissolved humic material: Binding and dissociation. Environ Sci Technol 19:1072-1076.
3. Gauthier TD, Seitz WR, Grant CL. 1987. Effects of structural and compositional variations of dissolved humic materials on pyrene Koc values. Environ Sci Technol 21:243-248.
4. Carter CW, Suffet IH. 1982. Binding of DDT to dissolved humic materials. Environ Sci Technol 16:735-740.
5. Schlautman MA, Morgan JJ. 1993. Effects of aqueous chemistry on the binding of polycyclic aromatic hydrocarbons by dissolved humic materials. Environ Sci Technol 27:961-969.
6. Chiou CT, Malcolm RL, Brinton TI, Kile DE. 1986. Water solubility enhancement of some organic pollutants and pesticides by dissolved humic and fulvic acid. Environ Sci Technol 20:502-508.
7. Clapp CE, Mingelgrin U, Liu R, Zhang H, Hayes MHB. 1997. A quantitative estimation of the complexation of small organic molecules with soluble humic acids. J Environ Qual 26:1277-1281.
8. Karthikeyan KG, Chorover J. 2000. Effects of solution chemistry on the oxidative transformation of 1-naphthol and its complexation with humic acid. Environ Sci Technol 34:2939-2946.
9. Kopinke F-D, Georgi A, Mackenzie K. 2001. Sorption of pyrene to dissolved humic substances and related model polymers. 1. Structure-property correlation. Environ Sci Technol 35:2536-2542.
10. Ragle CS, Engebretson RR, von Wandruszka RMA. 1997. The sequestration of hydrophobic micropollutants by dissolved humic acids. Soil Sci 162:106-114.
11. Engebretson RR, von Wandruszka RMA. 1994. Microorganization in dissolved humic acids. Environ Sci Technol 28:1934-1941.
12. Kukkonen J, Oikari A. 1991. Bioavailability of organic pollutants in boreal waters with varying levels of dissolved organic material. Water Res 25:455-463.
13. Haitzer M, Hoss S, Traunspurger W, Steinberg C. 1999. Relationship between concentration of dissolved organic matter (DOM) and the effect of DOM on the bioconcentration of benzo[a]pyrene. Aquat Toxicol (NY) 45:147-158.
14. Taylor E Jr, Cook BB, Tarr MA. 1999. Dissolved organic matter inhibition of sonochemical degradation of aqueous polycyclic aromatic hydrocarbons. Ultrason Sonochem 6:175-183.
15. Kan AT, Tomson MB. 1990. Ground water transport of hydrophobic organic compounds in the presence of dissolved organic matter. Environ Toxicol Chem 9:253-263.
16. Chin Y-P, Aiken GR, Danielsen KM. 1997. Binding of pyrene to aquatic and commercial humic substances: The role of molecular weight and aromaticity. Environ Sci Technol 31:1630-1635.
17. Backhus DA, Gschwend PM. 1990. Fluorescent polycyclic aromatic hydrocarbons as probes for studying the impact of colloids on pollutant transport in groundwater. Environ Sci Technol 24: 1214-1223.
18. Gauthier TD, Shane EC, Guerin WF, Seitz WR, Grant CL. 1986. Fluorescence quenching method for determining equilibrium constants for polycyclic aromatic hydrocarbons binding to dissolved humic materials. Environ Sci Technol 20:1162-1166.
19. Morra MJ, Corapcioglu MO, von Wandruszka RMA, Marshall DB, Topper K. 1990. Fluorescence quenching and polarization studies of naphthalene and 1-naphthol interaction with humic acid. Soil Sci Soc Am J 54:1283-1289.
20. Kosian PA, Hoke RA, Ankley GT, Vandermeiden FM. 1995. Determination of dieldrin binding to dissolved organic material in sediment pore-water using a reverse-phase separation technique. Environ Toxicol Chem 14:445-450.
21. Ridal JJ, Fox ME, Sullivan CA, Maguire RJ, Mazumder A, Lean DRS. 1997. Evaluation of automated extraction of organochlorine contaminants from freshwater. Anal Chem 69:711-717.
22. Dixon AM, Mai MA, Larive CK. 1999. NMR investigation of the interactions between 4′-fluoro- 1′ -acetonaphthone and the Suwannee River fulvic acid. Environ Sci Technol 33:958-964.
23. 13C NMR spectroscopy techniques to study the interaction of pollutants with humic substances. In Nanny MA, Minear RA, Leenheer JA, eds, Nuclear Magnetic Resonance Spectroscopy in Environmental Chemistry. Oxford University Press, New York, NY, USA, pp 26-50.
24. 1 relaxation measurements. Environ Sci Technol 31:530-534.
25. Nanny MA. 1999. Deuterium NMR characterization of noncovalent interactions between monoaromatic compounds and fulvic acids. Organ Geochem 30:901-909.
26. 1 relaxation study. Environ Sci Technol 35:379-384.
27. Hatcher PG, Bortiatynski JM, Minard RD, Dec J, Bollag J-M. 1993. Use of high-resolution carbon-13 NMR to examine the enzymatic covalent binding of carbon-13-labeled 2,4-dichlorophenol to humic substances. Environ Sci Technol 27:2098-2103.
28. Danielsen KM, Chin Y-P, Buterbaugh JS, Gustafson TL, Traina SJ. 1995. Solubility enhancement and fluorescence quenching of pyrene by humic substances - The effect of dissolved-oxygen on quenching processes. Environ Sci Technol 29:2162-2165.
29. Swift RS. 1996. Organic matter characterization. In Sparks DL, ed, Methods of Soil Analysis, Part 3 - Chemical Methods. Soil Science Society of America, Madison, WI, pp 1011-1069.
30. 13C NMR spectroscopy to geochemical studies of humic substances. In Hayes MHB, Mac Carthy P, Malcolm RL, Swift RS, eds, Humic Substances H. In Search of Structure. John Wiley, New York, NY, USA, pp 340-372.
31. Simpson AJ. 2001. Multidimensional solution state NMR of humic substances: A practical guide and review. Soil Sci 166:795-809.
32. Simpson AJ, Burdon J, Graham CL, Hayes MHB, Spencer N, Kingery WL. 2001. Interpretation of heteronuclear and multidimensional NMR spectroscopy of humic substances. Eur J Soil Sci 52:495-509.
33. Salloum MJ, Dudas MJ, McGill WB. 2001. Variation of 1-naphthol sorption with organic matter fractionation: The role of physical conformation. Organ Geochem 32:709-719.
34. Simpson AJ, Kingery WL, Spraul M, Humpfer E, Dvortsak P, Kerssebaum R. 2001. Separation of structural components in soil organic matter by diffusion ordered spectroscopy. Environ Sci Technol 35:4421-4425.
35. Simpson AJ, Boersma RE, Kingery WL, Hicks RP, Hayes MHB. 1997. Applications of NMR spectroscopy for studies of the molecular compositions of humic substances. In Hayes MHB, Wilson WS, eds, Humic Substances in Peats and Sludges. The Royal Society of Chemistry, Cambridge, UK, pp 46-62.
36. 1 NMR relaxation times of quinolines as a function of temperature in liquid and supercooled liquid state. J Mol Liq 85:77-86.
37. Perminova IV, Grechishcheva NY, Petrosyan VS. 1999. Relationships between structure and binding affinity of humic substances for polycyclic aromatic hydrocarbons: Relevance of molecular descriptors. Environ Sci Technol 33:3781-3787.
38. Murphy EM, Zachara JM, Smith SC. 1990. Influence of mineral-bound humic substances on the sorption of hydrophobic organic compounds. Environ Sci Technol 24:1507-1516.
39. 2H NMR investigation of the interaction between nonionic organic contaminants and dissolved humic material. In Nanny MA, Minear RA, Leenheer JA, eds, Nuclear Magnetic Resonance Spectroscopy in Environmental Chemistry. Oxford University Press, New York, NY, USA, pp 73-90.
40. 1H HR-MAS NMR spectroscopy for the study of structures and associations of organic components at the solid-aqueous interface of a whole soil. Environ Sci Technol 35:3321-3325.