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pH and ionic strength effects on the binding constant between a nitrogen-containing polycyclic aromatic compound and humic acid

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Abstract

Polycyclic aromatic compounds (PACs) are widespread environmental pollutants with a high potential to act as human carcinogens and mutagens. The behavior of PACs is significantly affected by their interactions with dissolved organic matter (DOM), such as their transport, solubility, bioavailability, and bioaccumulation in the aquatic environment. Being a basic PAC, benzo(h)quinoline (BQ) is the dominant species, as the solution’s pH value is higher than BQ’s pK a (pK a of BQ = 4.2). In contrast, benzo(h)quinolinium (BQH+) is the major species, as the solution’s pH value is lower than its pK a. The binding constant (K DOC), measured by fluorescence quenching, between BQ/BQH+ and Leonardite humic acid (LHA) would decrease 70 to 95 % and 20 to 90 % when increasing the ionic strength in acidic and neutral to basic conditions, respectively. The results can be attributed to the added cation (Na+ and Mg2+), which forms a bridge with LHA and enhances the intramolecular reaction among these functional groups, therefore inducing the coiling up within the LHA molecule. In addition, the decrease of the K DOC with added MgCl2/MgSO4 (75–95 %) is higher than that with added NaCl/Na2SO4 (20–75 %), indicating that the K DOC was affected by the charge density of cations. The fluorescence intensity of BQH+ in the absence of LHA (F 0) was found to decay only in the acidic solution with Cl, suggesting that Cl might be a heavy atom serving as a quencher in an acidic solution.

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References

  • Bejarano AC, Decho AW, Chandler GT (2005) The role of various dissolved organic matter forms on chlorpyrifos bioavailability to the estuarine bivalve Mercenaria mercenaria. Mar Environ Res 60:111–130

    Article  CAS  Google Scholar 

  • Buryskova B, Hilscherova K, Blaha L, Marsalek B, Holoubek I (2006) Toxicity and modulations of biomarkers in Xenopus laevis embryos exposed to polycyclic aromatic hydrocarbons and their N-heterocyclic derivatives. Environ Toxicol 21:590–598

    Article  CAS  Google Scholar 

  • Carter CW, Suffet IH (1982) Binding of DDT to dissolved humic materials. Environ Sci Technol 16:735–740

    Article  CAS  Google Scholar 

  • De Schamphelaere KAC, Janssen CR (2002) A biotic ligand model predicting acute copper toxicity for Daphnia magna: the effects of calcium, magnesium, sodium, potassium, and pH. Environ Sci Technol 36:48–54

    Article  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • Hsieh P-C, Hsu S-H, Lee C-L, Brimblecombe P (2010) The pH dependence of binding benzo(h)quinoline and humic acid and effects on fluorescence quenching. Environ Toxicol Chem 29:1696–1702

    CAS  Google Scholar 

  • Hsieh PC, Brimblecombe P, Lee CL, Hsu SH (2012) The role of the characteristics of humic substances in binding with benzo h quinoline. Environ Toxicol Chem 31:246–252

    Article  CAS  Google Scholar 

  • Jones KD, Tiller CL (1999) Effect of solution chemistry on the extent of binding of phenanthrene by a soil humic acid: a comparison of dissolved and clay bound humic. Environ Sci Technol 33:580–587

    Article  CAS  Google Scholar 

  • Karthikeyan KG, Chorover J (2002) Humic acid complexation of basic and neutral polycyclic aromatic compounds. Chemosphere 48:955–964

    Article  CAS  Google Scholar 

  • Kim I, Lee M, Wang S (2014) Heavy metal removal in groundwater originating from acid mine drainage using dead Bacillus drentensis sp immobilized in polysulfone polymer. J Environ Manage 146:568–574

    Article  CAS  Google Scholar 

  • Komnitsas K, Zaharaki D (2014) Assessment of human and ecosystem risk due to agricultural waste compost application on soils: a review. Environ Forensics 15:312–328

    Article  Google Scholar 

  • Kuo LJ, Lee CL (2005) Stage change in binding of pyrene to selected humic substances under different ionic strengths. Environ Toxicol Chem 24:886–894

    Article  CAS  Google Scholar 

  • Lakowicz JR (1983) Principles of fluorescence spectroscopy. Plenum Press, New York, NY, USA

    Book  Google Scholar 

  • Lee ML, Novotny MV, Bartle KD (1981) Analytical chemistry of polycyclic aromatic compounds. Academic, New York

    Google Scholar 

  • Lee C-L, Kuo L-J, Wang H-L, Hsieh P-C (2003) Effects of ionic strength on the binding of phenanthrene and pyrene to humic substances: three-stage variation model. Water Res 37:4250–4258

    Article  CAS  Google Scholar 

  • Li XP, McGuffin VL (2004) Selective fluorescence quenching of nitrogen-containing polycyclic aromatic hydrocarbons by aliphatic amines. Anal Chim Acta 526:155–162

    Article  CAS  Google Scholar 

  • Marschner B, Winkler R, Jodemann D (2005) Factors controlling the partitioning of pyrene to dissolved organic matter extracted from different soils. Eur J Soil Sci 56:299–306

    Article  CAS  Google Scholar 

  • Murphy EM, Zachara JM, Smith SC, Phillips JL, Wietsma TW (1994) Interaction of hydrophobic organic-compounds with mineral-bound humic substances. Environ Sci Technol 28:1291–1299

    Article  CAS  Google Scholar 

  • Nebbioso A, Piccolo A (2013) Molecular characterization of dissolved organic matter (DOM): a critical review. Anal Bioanal Chem 405:109–124

    Article  CAS  Google Scholar 

  • Palmer NE, von Wandruszka R (2001) Dynamic light scattering measurements of particle size development in aqueous humic materials. Fresenius’ J Anal Chem 371:951–954

    Article  CAS  Google Scholar 

  • Raber B, Kogel-Knabner I, Stein C, Klem D (1998) Partitioning of polycyclic aromatic hydrocarbons to dissolved organic matter from different soils. Chemosphere 36:79–97

    Article  CAS  Google Scholar 

  • Ragle CS, Engebretson RR, vonWandruszka R (1997) The sequestration of hydrophobic micropollutants by dissolved humic acids. Soil Sci 162:106–114

    Article  CAS  Google Scholar 

  • Rudnicki P, Hubicki Z, Kolodynska D (2014) Evaluation of heavy metal ions removal from acidic waste water streams. Chem Eng J 252:362–373

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • Shannon RD (1976) Revised effective ionic radii and systematic studies of interatomic distances in halides and chalcogenides. Acta Crystallogr Sect A 32:751–767

    Article  Google Scholar 

  • Shiu R-F, Chin W-C, Lee C-L (2014) Carbonaceous particles reduce marine microgel formation. Sci Rep 4:1–6

    Article  Google Scholar 

  • Sparks DL (1995) Environmental soil chemistry. Academic, San Diego

    Google Scholar 

  • Tombacz E (1999) Colloidal properties of humic acids and spontaneous changes of their colloidal state under variable solution conditions. Soil Sci 164:814–824

    Article  CAS  Google Scholar 

  • von Wandruszka R, Ragle C, Engebretson R (1997) The role of selected cations in the formation of pseudomicelles in aqueous humic acid. Talanta 44:805–809

    Article  Google Scholar 

  • Zepp RG, Sheldon WM, Moran MA (2004) Dissolved organic fluorophores in southeastern US coastal waters: correction method for eliminating Rayleigh and Raman scattering peaks in excitation–emission matrices. Mar Chem 89:15–36

    Article  CAS  Google Scholar 

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Acknowledgements

We gratefully appreciate Caroline Brimblecombe for proofreading this manuscript and for her helpful discussions. We thank the Ministry of Science and Technology, Ministry of Education of Taiwan, and the Research Center of Environmental Medicine for providing financial support for this research under contract NSC 101-2611-M-110-012, DOE 01C030203, and KMU-TP103A27. The authors also appreciate the reviewers’ valuable comments to improve the quality of this article.

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This chapter does not contain any studies with human participants or animals performed by any of the authors.

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Correspondence to Chon-Lin Lee.

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Responsible editor: Philippe Garrigues

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Chang, KC., Lee, CL., Hsieh, PC. et al. pH and ionic strength effects on the binding constant between a nitrogen-containing polycyclic aromatic compound and humic acid. Environ Sci Pollut Res 22, 13234–13242 (2015). https://doi.org/10.1007/s11356-015-4392-z

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