π+-π Interactions between (hetero)aromatic amine cations and the graphitic surfaces of pyrogenic carbonaceous materials

Environmental Science and Technology

Volumn 49, Issue 2, 2015, Pages 906-914

  Xiao, Feng ^a   Pignatello, Joseph J ^a  

^a Department of Environmental Sciences Connecticut Agricultural Experimental Station ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; AROMATIC COMPOUNDS; AROMATIZATION; DENSITY FUNCTIONAL THEORY; FREE ENERGY; GRAPHENE; GRAPHITE; HYDROPHOBICITY; NAPHTHALENE; ORGANIC COMPOUNDS; POSITIVE IONS;

CARBONACEOUS MATERIALS; CHARGE DELOCALIZATION; ELECTRON DONOR ACCEPTORS; ELECTROSTATIC POTENTIALS; ENVIRONMENTAL CONCERNS; FREE ENERGY OF ADSORPTION; HETEROCYCLIC AROMATIC AMINES; SUBSTITUTED ANILINES;

AMINES;

2 4 DINITROBENZENE; ADSORBENT; ALKYL GROUP; ANILINE; AROMATIC AMINE; BENZENE DERIVATIVE; BIOCHAR; BLACK CARBON; CATION; GRAPHENE; GRAPHITE; HERBICIDE; HETEROCYCLIC AMINE; NAPHTHALENE; PYROGENIC CARBONACEOUS MATERIAL; QUINOLINIUM ION; TRIAZINE; UNCLASSIFIED DRUG; 2,4-DINITROBENZENE; AMETRYN; AMINE; CARBON; CHARCOAL; NAPHTHALENE DERIVATIVE; NITROBENZENE DERIVATIVE; ORGANIC COMPOUND; TERBUTRYN; TRIAZINE DERIVATIVE;

ADSORPTION; GRAPHITE; HYDROPHOBICITY; PH; POLARIZATION;

ADSORPTION; ARTICLE; CHARGE POLARIZATION; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; ELECTRON; ELECTRON TRANSPORT; HYDROPHOBICITY; IONIC STRENGTH; PH; POLARIZATION; STATIC ELECTRICITY; CHEMICAL PHENOMENA; CHEMISTRY; THERMODYNAMICS;

ADSORPTION; AMINES; CARBON; CATIONS; CHARCOAL; DINITROBENZENES; ELECTRONS; GRAPHITE; HYDROGEN-ION CONCENTRATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; NAPHTHALENES; ORGANIC CHEMICALS; STATIC ELECTRICITY; THERMODYNAMICS; TRIAZINES;

EID: 84921785501     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es5043029     Document Type: Article

References (51)

1. Lehmann, J.; Joseph, S. Biochar for Environmental Management: Science and Technology; Earthscan Publications Ltd.: London, UK, 2009.
2. Shen, G. F.; Wei, S. Y.; Wei, W.; Zhang, Y. Y.; Min, Y. J.; Wang, B.; Wang, R.; Li, W.; Shen, H. Z.; Huang, Y.; Yang, Y. F.; Wang, W.; Wang, X. L.; Wang, X. J.; Tao, S. Emission factors, size distributions, and emission inventories of carbonaceous particulate matter from residential wood combustion in rural China. Environ. Sci. Technol. 2012, 46 (7), 4207-4214.
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: Hoboken, NJ, 2011; pp 3-50.
4. Luthy, R. G.; Aiken, G. R.; Brusseau, M. L.; Cunningham, S. D.; Gschwend, P. M.; Pignatello, J. J.; Reinhard, M.; Traina, S. J.; Weber, W. J.; Westall, J. C. Sequestration of hydrophobic organic contaminants by geosorbents. Environ. Sci. Technol. 1997, 31 (12), 3341-3347.
5. Cornelissen, G.; Gustafsson, O.; Bucheli, T. D.; Jonker, M. T. O.; Koelmans, A. A.; Van Noort, P. C. M. Extensive sorption of organic compounds to black carbon, coal, and kerogen in sediments and soils: Mechanisms and consequences for distribution, bioaccumulation, and biodegradation. Environ. Sci. Technol. 2005, 39 (18), 6881-6895.
6. Accardi-Dey, A.; Gschwend, P. M. Assessing the combined roles of natural organic matter and black carbon as sorbents in sediments. Environ. Sci. Technol. 2002, 36 (1), 21-29.
7. Kookana, R. S. The role of biochar in modifying the environmental fate, bioavailability, and efficacy of pesticides in soils: A review. Aust J. Soil Res. 2010, 48 (6-7), 627-637.
8. Yang, Y. N.; Sheng, G. Y. Enhanced pesticide sorption by soils containing particulate matter from crop residue burns. Environ. Sci. Technol. 2003, 37 (16), 3635-3639.
9. Crittenden, J. C.; Vaitheeswaran, K.; Hand, D. W.; Howe, E. W.; Aieta, E. M.; Tate, C. H.; Mcguire, M. J.; Davis, M. K. Removal of dissolved organic-carbon using granular activated carbon. Water Res. 1993, 27 (4), 715-721.
10. Li, Q. L.; Snoeyink, V. L.; Marinas, B. J.; Campos, C. Pore blockage effect of NOM on atrazine adsorption kinetics of PAC: The roles of PAC pore size distribution and NOM molecular weight. Water Res. 2003, 37 (20), 4863-4872.
11. Cho, Y. M.; Ghosh, U.; Kennedy, A. J.; Grossman, A.; Ray, G.; Tomaszewski, J. E.; Smithenry, D. W.; Bridges, T. S.; Luthy, R. G. Field application of activated carbon amendment for in-situ stabilization of polychlorinated biphenyls in marine sediment. Environ. Sci. Technol. 2009, 43 (10), 3815-3823.
12. Gilmour, C. C.; Riedel, G. S.; Riedel, G.; Kwon, S.; Landis, R.; Brown, S. S.; Menzie, C. A.; Ghosh, U. Activated carbon mitigates mercury and methylmercury bioavailability in contaminated sediments. Environ. Sci. Technol. 2013, 47 (22), 13001-13010.
13. Meynet, P.; Hale, S. E.; Davenport, R. J.; Cornelissen, G.; Breedveld, G. D.; Werner, D. Effect of activated carbon amendment on bacterial community structure and functions in a PAH impacted urban soil. Environ. Sci. Technol. 2012, 46 (9), 5057-5066.
14. Allen-King, R. M.; Grathwohl, P.; Ball, W. P. New modeling paradigms for the sorption of hydrophobic organic chemicals to heterogeneous carbonaceous matter in soils, sediments, and rocks. Adv. Water Resour 2002, 25 (8-12), 985-1016.
15. Keiluweit, M.; Kleber, M. Molecular-level interactions in soils and sediments: The role of aromatic π-systems. Environ. Sci. Technol. 2009, 43 (10), 3421-3429.
16. Zhu, D. Q.; Pignatello, J. J. Characterization of aromatic compound sorptive interactions with black carbon (charcoal) assisted by graphite as a model. Environ. Sci. Technol. 2005, 39 (7), 2033-2041.
17. Teixido, M.; Pignatello, J. J.; Beltran, J. L.; Granados, M.; Peccia, J. Speciation of the ionizable antibiotic sulfamethazine on black carbon (biochar). Environ. Sci. Technol. 2011, 45 (23), 10020-10027.
18. Ni, J. Z.; Pignatello, J. J.; Xing, B. S. Adsorption of aromatic carboxylate ions to black carbon (biochar) is accompanied by proton exchange with water. Environ. Sci. Technol. 2011, 45 (21), 9240-9248.
19. Chen, W.; Duan, L.; Zhu, D. Q. Adsorption of polar and nonpolar organic chemicals to carbon nanotubes. Environ. Sci. Technol. 2007, 41 (24), 8295-8300.
20. Lattao, C.; Cao, X. Y.; Mao, J. D.; Schmidt-Rohr, K.; Pignatello, J. J. Influence of molecular structure and adsorbent properties on sorption of organic compounds to a temperature series of wood chars. Environ. Sci. Technol. 2014, 48 (9), 4790-4798.
21. Zhu, D. Q.; Herbert, B. E.; Schlautman, M. A.; Carraway, E. R.; Hur, J. Cation-pi bonding: A new perspective on the sorption of polycyclic aromatic hydrocarbons to mineral surfaces. J. Environ. Qual 2004, 33 (4), 1322-1330.
22. Qu, X. L.; Liu, P.; Zhu, D. Q. Enhanced sorption of polycyclic aromatic hydrocarbons to tetra-alkyl ammonium modified smectites via cation-pi interactions. Environ. Sci. Technol. 2008, 42 (4), 1109-1116.
23. Vijay, D.; Sastry, G. N. The cooperativity of cation-π and π-π interactions. Chem. Phys. Lett. 2010, 485 (1-3), 235-242.
24. Singh, N. J.; Min, S. K.; Kim, D. Y.; Kim, K. S. Comprehensive energy analysis for various types of π-interaction. J. Chem. Theory Comput 2009, 5 (3), 515-529.
25. Wijnja, H.; Pignatello, J. J.; Malekani, K. Formation of π-π complexes between phenanthrene and model π-acceptor humic subunits. J. Environ. Qual 2004, 33 (1), 265-275.
26. Gilliom, R. J. Pesticides in U.S. streams and groundwater. Environ. Sci. Technol. 2007, 41 (10), 3407-3413.
27. Hoffman, R. S.; Capel, P. D.; Larson, S. J. Comparison of pesticides in eight U.S. urban streams. Environ. Toxicol. Chem. 2000, 19 (9), 2249-2258.
28. Stuermer, D. H.; Ng, D. J.; Morris, C. J. Organic contaminants in groundwater near an underground coal gasification site in northeastern Wyoming. Environ. Sci. Technol. 1982, 16 (9), 582-587.
29. Pereira, W. E.; Rostad, C. E.; Garbarino, J. R.; Hult, M. F. Groundwater contamination by organic bases derived from coal-tar wastes. Environ. Toxicol. Chem. 1983, 2 (3), 283-294.
30. Montgomery, J. H. Groundwater Chemicals Desk Reference, 4th ed.; CRC Press: Boca Raton, 2007.
31. Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Kawagoshi, Y. Organic components in leachates from hazardous waste disposal sites. Waste Manage Res. 1999, 17 (3), 186-197.
32. Wilkins, K.; Nielsen, E. M.; Wolkoff, P. Patterns in volatile organic compounds in dust from moldy buildings. Indoor Air 1997, 7 (2), 128-134.
33. Brumley, W. C.; Brownrigg, C. M.; Brilis, G. M. Characterization of nitrogen-containing aromatic compounds in soil and sediment by capillary gas-chromatography mass-spectrometry after fractionation. J. Chromatogr. 1991, 558 (1), 223-233.
34. Li, H.; Gao, Y.; Pan, L.; Zhang, Y.; Chen, Y.; Sun, Z. Electrosorptive desalination by carbon nanotubes and nanofibres electrodes and ion-exchange membranes. Water Res. 2008, 42 (20), 4923-4928.
35. Celik, E.; Park, H.; Choi, H.; Choi, H. Carbon nanotube blended polyethersulfone membranes for fouling control in water treatment. Water Res. 2011, 45 (1), 274-282.
36. Cao, X. Y.; Pignatello, J. J.; Li, Y.; Lattao, C.; Chappell, M. A.; Chen, N.; Miller, L. F.; Mao, J. D. Characterization of wood chars produced at different temperatures using advanced solid-state C-13 NMR spectroscopic techniques. Energy Fuel 2012, 26 (9), 5983-5991.
37. Xiao, F.; Pignatello, J. J. Effect of adsorption nonlinearity on the pH-adsorption profile of ionizable organic compounds. Langmuir 2014, 30 (8), 1994-2001.
38. USEPA. Product Properties Test Guidelines: Partition Coefficient (n-octanol/water) Shake Flask Method; U.S. Environmental Protection Agency Prevention Pesticides and Toxic Substances: Washington, DC, 1996.
39. http://www.syrres.com/what-we-do/databaseforms.aspx?id=386 (accessed January 2013-March 2014).
40. Wang, X. L.; Xing, B. S. Importance of structural makeup of biopolymers for organic contaminant sorption. Environ. Sci. Technol. 2007, 41 (10), 3559-3565.
41. Ahnert, F.; Arafat, H. A.; Pinto, N. G. A study of the influence of hydrophobicity of activated carbon on the adsorption equilibrium of aromatics in non-aqueous media. Adsorption 2003, 9 (4), 311-319.
42. Antizar-Ladislao, B.; Galil, N. I. Biosorption of phenol and chlorophenols by acclimated residential biomass under bioremediation conditions in a sandy aquifer. Water Res. 2004, 38 (2), 267-276.
43. Andrades, M. S.; Rodriguez-Cruz, M. S.; Sanchez-Martin, M. J.; Sanchez-Camazano, M. Effect of the addition of wine distillery wastes to vineyard soils on the adsorption and mobility of fungicides. J. Agric. Food Chem. 2004, 52 (10), 3022-3029.
44. Lotufo, G. R.; Lydy, M. J. Comparative toxicokinetics of explosive compounds in sheepshead minnows. Arch. Environ. Contam. Toxicol. 2005, 49 (2), 206-214.
45. Engtrakul, C.; Davis, M. F.; Gennett, T.; Dillon, A. C.; Jones, K. M.; Heben, M. J. Protonation of carbon single-walled nanotubes studied using C-13 and H-1-C-13 cross polarization nuclear magnetic resonance and Raman spectroscopies. J. Am. Chem. Soc. 2005, 127 (49), 17548-17555.
46. Heard, G. L.; Boyd, R. J. Calculation of quadrupole moments of polycyclic aromatic hydrocarbons: Applications to chromatography. J. Phys. Chem. A 1997, 101 (29), 5374-5377.
47. Hehre, W. J. A Guide to Molecular Mechanics and Quantum Chemical Calculations; Wavefunction: Irvine, CA, 2003.
48. Mecozzi, S.; West, A. P.; Dougherty, D. A. Cation-π interactions in simple aromatics: Electrostatics provide a predictive tool. J. Am. Chem. Soc. 1996, 118 (9), 2307-2308.
49. Mecozzi, S.; West, A. P.; Dougherty, D. A. Cation-π interactions in aromatics of biological and medicinal interest: Electrostatic potential surfaces as a useful qualitative guide. Proc. Natl. Acad. Sci. U.S.A. 1996, 93 (20), 10566-10571.
50. Cockroft, S. L.; Perkins, J.; Zonta, C.; Adams, H.; Spey, S. E.; Low, C. M. R.; Vinter, J. G.; Lawson, K. R.; Urch, C. J.; Hunter, C. A. Substituent effects on aromatic stacking interactions. Org. Biomol Chem. 2007, 5 (7), 1062-1080.
51. Johnson, C. A.; Westall, J. C. Effect of pH and KCl concentration on the octanol water distribution of methylanilines. Environ. Sci. Technol. 1990, 24 (12), 1869-1875.