Sorption selectivity in natural organic matter studied with nitroxyl paramagnetic relaxation probes

Environmental Science and Technology

Volumn 46, Issue 23, 2012, Pages 12814-12822

  Lattao, Charisma ^a   Cao, Xiaoyan ^b   Li, Yuan ^b   Mao, Jingdong ^b   Schmidt Rohr, Klaus ^c   Chappell, Mark A ^d   Miller, Lesley F ^d   Dela Cruz, Albert Leo ^e   Pignatello, Joseph J ^a  

^a Northeast Regional Center for Excellence in Vector Borne Diseases   (United States)

^b OLD DOMINION UNIVERSITY   (United States)

^c IOWA STATE UNIVERSITY   (United States)

^d U S ARMY ENGINEER RESEARCH AND DEVELOPMENT CENTER   (United States)

^e LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BULK CHEMICAL COMPOSITION; CHEMICAL ENVIRONMENT; HEXADECANE; METHYL ETHERS; MICRODOMAIN; NATURAL ORGANIC MATTERS; NMR SIGNALS; PARAMAGNETIC PROBES; PARAMAGNETIC RELAXATION; PREFERENTIAL SORPTION; ROTATIONAL MOBILITY; SORPTION SELECTIVITY; SORPTION SITES; SPIN INTERACTION; SPIN PROBE;

AROMATIC COMPOUNDS; BIOLOGICAL MATERIALS; CARBON; ELECTROSPINNING; ETHERS; FUNCTIONAL GROUPS; MAGNETIC MOMENTS; NUCLEAR MAGNETIC RESONANCE; ORGANIC SOLVENTS; PARAFFINS; PARAMAGNETISM; POLYSTYRENES; SORPTION; TOLUENE;

PROBES;

2,2,6,6 TETRAMETHYLPIPERIDINE 1 OXYL; ANISOLE; CARBON 13; CELLULOSE; HEXADECANE; NATURAL ORGANIC MATTER; OCTANOL; PIPERIDINE DERIVATIVE; POLYMER; POLYSTYRENE POLY(VINYL METHYL ETHER); TEMPOL; TOLUENE; UNCLASSIFIED DRUG;

CHEMICAL COMPOSITION; ELECTRON SPIN RESONANCE; NUCLEAR MAGNETIC RESONANCE; ORGANIC MATTER; PROBE; SORPTION;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE;

ADSORPTION; COAL; CYCLIC N-OXIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; MAGNETIC RESONANCE SPECTROSCOPY; NITROGEN OXIDES; POLYSTYRENES; POLYVINYLS; SOIL; SPIN LABELS;

EID: 84870490219     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es302157j     Document Type: Article

References (47)

1. Pignatello, J. J. Dynamic interactions of natural organic matter and organic compounds J. Soils Sediments 2012, 10.1007/s11368-012-0490-4
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. Pignatello, J. J. Interactions of anthropogenic organic chemicals with natural organic matter and black carbon in environmental particles. In Biophysico-Chemical Processes of Anthropogenic Organic Compounds in Environmental Systems; Xing, B.; Senesi, N.; Huang, P. M., Eds.; J. Wiley & Sons: NJ, 2011; pp 3-50.
4. Zhu, D.; Pignatello, J. J. A concentration-dependent multi-term linear free energy relationship for sorption of organic compounds to soils based on the hexadecane dilute-solution reference state Environ. Sci. Technol. 2005, 39, 8817-8828
5. Endo, S.; Grathwohl, P.; Haderlein, S. B.; Schmidt, T. C. Compound-specific factors influencing sorption nonlinearity in natural organic matter Environ. Sci. Technol. 2008, 42, 5897-5903
6. Borisover, M.; Graber, E. R. Classifying NOM-organic sorbate interactions using compound transfer from an inert solvent to the hydrated sorbent Environ. Sci. Technol. 2003, 37, 5657-5664
7. Mao, J.-D.; Hundal, L. S.; Thompson, M. L.; Schmidt-Rohr, K. Correlation of poly(methylene)-rich amorphous aliphatic domains in humic substances with sorption of a nonpolar organic contaminant, phenanthrene Environ. Sci. Technol. 2002, 36, 929-936
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. Mao, J.; Schmidt-Rohr, K. Absence of mobile carbohydrate domains in dry humic substances proven by NMR, and implications for organic-contaminant sorption models Environ. Sci. Technol. 2006, 40, 1751-1756
10. Lattao, C.; Birdwell, J.; Wang, J. J.; Cook, R. L. Studying organic matter molecular assemblage within a whole organic soil by nuclear magnetic resonance J. Environ. Qual. 2008, 37, 1501-1509
11. 13C NMR characterization of humic acids from soils of a development sequence J. Soil Sci. 1991, 42, 39-46
12. 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
13. Karapanagioti, H. K.; Childs, J.; Sabatini, D. A. Impacts of heterogeneous organic matter on phenanthrene sorption: Different soil and sediment samples Environ. Sci. Technol. 2001, 35, 4684-4690
14. http://web.anl.gov/PCS/pcshome.html.
15. Gustafsson, O.; Bucheli, T. D.; Kukulska, Z.; Andersson, M.; Largeau, C.; Rouzaud, J.-N.; Reddy, C. M.; Eglinton, T. I. Evaluation of a protocol for the quantification of black carbon in sediments Global Biogeochem. Cycles 2001, 15, 881-890
16. 13C Solid-state NMR of Argonne premium coals Energy Fuels 1989, 3, 187-193
17. DuBose, S. B.; Wertz, D. L. X-ray analysis of coals treated with organic liquids. Detailed study of the adduct formed between pyridine molecules and Beulah-Zap lignite Energy Fuels 2002, 16, 669-675
18. Bertini, I.; Luchinat, C.; Aime, S. Chapter 3. Relaxation Coord. Chem. Rev. 1996, 150, 77-110
19. 13C CP/MAS NMR spectrum of a de-ashed soil Geoderma 1999, 89, 219-248
20. Koptyug, I. V.; Bossmann, S. H.; Turro, N. J. Inversion-recovery of nitroxide spin labels in solution and microheterogeneous environments J. Am. Chem. Soc. 1996, 118, 1435-1445
21. Franchi, P.; Lucarini, M.; Pedrielli, P.; Pedulli, G. F. Nitroxide radicals as hydrogen bonding acceptors. An infrared and EPR study Chem. Phys. Chem. 2002, 3, 78-793
22. Endo, K.; Morishima, I.; Yonezawa, T. Use of a stable free radical as a NMR spin probe for studying intermolecular interactions. XIV. A proton relaxation study of the hydrogen bond involving a stable free radical J. Chem. Phys. 1977, 67, 4760-4767
23. Pace, M. D.; Snow, A. W. Nitroxide spin probe/label study of hydrogen bonding and probe size effects in a linear epoxy polymer Macromolecules 1995, 28, 5300-5305
24. Satterlee, J. D. Fundamental concepts of NMR in paramagnetic systems part II: Relaxation effects Concept Magnetic Res. 1990, 2, 119-129
25. 13C correlation solid-state nuclear magnetic resonance Environ. Sci. Technol. 2001, 35, 1928-1934
26. Morishima, I.; Endo, K.; Yonezawa, T. Interaction between closed-shell and open-shell molecules. 6. H-1 and C-13 contact shifts and molecular-orbital studies on hydrogen-bond of nitroxide radical J. Chem. Phys. 1973, 58, 3146-3154
27. 13C CPMAS NMR study of samples of four organic soils Geoderma 1984, 33, 245-453
28. Lee, S.; Sung, C. S. P. Surface chemical composition analysis in polystyrene/poly(vinyl methyl ether) blend films by UV reflection spectroscopy Macromolecules 2001, 34, 599-604
29. Braida, W. J.; Pignatello, J. J.; Lu, Y.; Ravikovitch, P. I.; Neimark, A. V.; Xing, B. Sorption hysteresis of benzene in charcoal particles Environ. Sci. Technol. 2003, 37, 409-417
30. Forrester, A. R.; Hay, J. M.; Thomson, R. H. Organic Chemistry of Stable Free Radicals; Academic Press: London and New York, 1968; p 225.
31. Guidelines for The Testing of Chemicals, OECD 107, Partition Coefficient (n-octanol/water) (Flask-shaking Method); Organization for Economic Cooperation and Development: Paris, France.
32. Dixon, W. T. Total suppression of sidebands in CPMAS C-13 NMR J. Magn. Reson. 1982, 49, 341-345
33. Bowry, V. W.; Ingold, K. U. Kinetics of nitroxide radical trapping. 2. Structural effects J. Am. Chem. Soc. 1992, 114, 4992-4996
34. Ottaviani, M. F.; Garcia-Garibay, M.; Turro, N. J. TEMPO radicals as EPR probes to monitor the adsorption of different species into X xeolite Colloids Surf., A 1992, 72, 321-332
35. Dumestre, A.; McBride, M.; Baveye, P. Use of EPR to monitor the distribution and availability of organic xenobiotics in model soil systems Environ. Sci. Technol. 2000, 34, 1259-1264
36. Demond, A. H.; Lindner, A. S. Estimation of interfacial tension between organic liquids and water Environ. Sci. Technol. 1993, 27, 2318-2331
37. Akim, E. L. Cellulose-bellwether or old hat Chem. Tech. 1978, 8, 676-682
38. Almeida, L. E.; Borissevitch, I. E.; Yushmanov, V. E.; Tabak, M. Different micellar packing and hydrophobicity of the membrane probes TEMPO and TEMPOL influence their partition between aqueous and micellar phases rather than location in the micelle interior J. Colloid Interface Sci. 1998, 203, 456-463
39. Pegi, A.; Julijana, K.; Slavko, P.; Janez, S.; Marjeta, S. The Effect of lipophilicity of spin-labeled compounds on their distribution in solid lipid nanoparticle dispersions studied by electron paramagnetic resonance J. Pharm. Sci. 2003, 92, 58-66
40. Abraham, M. H.; Chadha, H. S.; Whiting, G. S.; Mitchell, R. C. Hydrogen bonding. 32. An analysis of water-octanol and water-alkane partitioning and the Δlog P parameter of Seiler J. Pharm. Sci. 1994, 83, 1085-1100
41. Bank, M.; Leffingwell, J.; Thies, C. The influence of solvent upon the compatibility of polystyrene and poly (vinyl methyl ether) Macromolecules 1971, 4, 43-46
42. Caravatti, P.; Neuenschwander, P.; Emst, R. R. Characterization of polymer blends by selective proton spin-diffusion nuclear magnetic resonance measurements Macromolecules 1986, 19, 1889-1895
43. Schmidt-Rohr, K.; Clauss, J.; Spiess, H. W. Correlation of structure, mobility, and morphological information in heterogeneous polymer materials by 2-Dimensional Wideline-Separation NMR spectroscopy Macromolecules 1992, 25, 3273-3277
44. Pignatello, J. J.; Kwon, S.; Lu, Y. Effect of natural organic substances on the surface and adsorptive properties of environmental black carbon (char): Attenuation of surface activity by humic and fulvic acids Environ. Sci. Technol. 2006, 40, 7757-7763
45. 2-probed surface properties of natural sorbents Environ. Sci. Technol. 2005, 39, 7932-7939
46. Oen, A. M. P.; Beckingham, B.; Ghosh, U.; Kruså, M. E.; Luthy, R. G.; Hartnik, T.; Henriksen, T.; Cornelissen, G. Sorption of organic compounds to fresh and field-aged activated carbons in soils and sediments Environ. Sci. Technol. 2012, 46, 810-817
47. Larsen, J. W.; Hall, P.; Wernett, P. C. Pore structure of the Argonne premium coal Energy Fuels 1995, 9, 324-330