Thermodynamic Study on the Protonation Reactions of Glyphosate in Aqueous Solution: Potentiometry, Calorimetry and NMR spectroscopy

Journal of Physical Chemistry B

Volumn 120, Issue 9, 2016, Pages 2132-2137

  Liu, Bijun ^a   Dong, Lan ^a   Yu, Qianhong ^a   Li, Xingliang ^a   Wu, Fengchang ^b   Tan, Zhaoyi ^a   Luo, Shunzhong ^a  

^a RESEARCH CENTER OF LASER FUSION   (China)

^b CHINESE RESEARCH ACADEMY OF ENVIRONMENTAL SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CALORIMETERS; CALORIMETRY; CARBOXYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POTENTIOMETERS (ELECTRIC MEASURING INSTRUMENTS); PROTONATION; SOLUTIONS; THERMODYNAMIC PROPERTIES;

CHEMICAL AND PHYSICAL PROPERTIES; CHEMICAL PROCESS; INFORMATION CONCERNING; PHOSPHONATE GROUP; PROTONATED SITES; PROTONATION REACTIONS; PROTONATION SITE; THERMODYNAMIC STUDIES;

HERBICIDES;

GLYCINE; GLYPHOSATE; HERBICIDE; PROTON; SOLUTION AND SOLUBILITY; WATER;

ANALOGS AND DERIVATIVES; CALORIMETRY; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POTENTIOMETRY; PROCEDURES; SOLUTION AND SOLUBILITY; THERMODYNAMICS;

CALORIMETRY; GLYCINE; HERBICIDES; MAGNETIC RESONANCE SPECTROSCOPY; POTENTIOMETRY; PROTONS; SOLUTIONS; THERMODYNAMICS; WATER;

EID: 84961143179     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/acs.jpcb.5b11550     Document Type: Article

References (41)

1. Ramstedt, M.; Norgren, C.; Sheals, J.; Boström, D.; Sjöberg, S.; Persson, P. Thermodynamic and Spectroscopic Studies of Cadmium(II)-N-(Phosphonomethyl)glycine (PMG) Complexes Inorg. Chim. Acta 2004, 357, 1185-1192 10.1016/j.ica.2003.10.029
2. Purgel, M.; Takács, Z.; Jonsson, C. M.; Nagy, L.; Andersson, I.; Bányai, I.; Pápai, I.; Persson, P.; Sjöberg, S.; Tóth, I. Glyphosate Complexation to Aluminium(III). An Equilibrium and Structural Study in Solution Using Potentiometry, Multinuclear NMR, ATR-FTIR, ESI-MS and DFT Calculations J. Inorg. Biochem. 2009, 103, 1426-1438 10.1016/j.jinorgbio.2009.06.011
3. Sagatys, D. S.; Dahlgren, C.; Smith, G.; Bott, R. C.; Willis, A. C. Metal Complexes with N-(Phosphonomethyl)glycine (Glyphosate): The Preparation and Characterization of the Group 2 Metal Complexes with Glyphosate and the Crystal Structure of Barium Glyphosate Dihydrate Aust. J. Chem. 2000, 53, 77-81 10.1071/CH99160
4. Heineke, D.; Franklin, S. J.; Raymond, K. N. Coordination Chemistry of Glyphosate: Structural and Spectroscopic Characterization of Bis(glyphosate)metal(III) Complexes Inorg. Chem. 1994, 33, 2413-2421 10.1021/ic00089a017
5. Glass, R. L. Metal Complex Formation by Glyphosate J. Agric. Food Chem. 1984, 32, 1249-1253 10.1021/jf00126a010
6. Subramaniam, V.; Hoggard, P. E. Metal Complexes of Glyphosate J. Agric. Food Chem. 1988, 36, 1326-1329 10.1021/jf00084a050
7. Bernards, M. L.; Thelen, K. D.; Penner, D.; Muthukumaran, R. B.; McCracken, J. L. Glyphosate Interaction with Manganese in Tank Mixtures and Its Effect on Glyphosate Absorption and Translocation Weed Sci. 2005, 53, 787-794 10.1614/WS-05-043R.1
8. Borggaard, O. K.; Gimsing, A. L. Fate of Glyphosate in Soil and the Possibility of Leaching to Ground and Surface Waters: A Review Pest Manage. Sci. 2008, 64, 441-456 10.1002/ps.1512
9. Sandberg, C. l.; Meggitt, W. F.; Penner, D. Adsorption, Mobility, and Microbial Degradation of Glyphosate in the Soil Weed Sci. 1975, 23, 229-234
10. Menelaou, M.; Dakanali, M.; Raptopoulou, C. P.; Drouza, C.; Lalioti, N.; Salifoglou, A. pH-Specific Synthetic Chemistry, and Spectroscopic, Structural, Electrochemical and Magnetic Susceptibility Studies in Binary Ni(II)-(carboxy)phosphonate Systems Polyhedron 2009, 28, 3331-3339 10.1016/j.poly.2009.05.084
11. 2 Fixation and Nickel Concentration in Glyphosate-Resistant Soybeans Appl. Soil Ecol. 2010, 44, 176-180 10.1016/j.apsoil.2009.12.003
12. Khalfa, A.; Ferrari, M.; Fournet, R.; Sirjean, B.; Verdier, L.; Glaude, P. A. Quantum Chemical Study of the Thermochemical Properties of Organophosphorous Compounds J. Phys. Chem. A 2015, 119, 10527-10539 10.1021/acs.jpca.5b07071
13. Abate, L.; Mineo, P.; Rigano, C.; Daniele, P.; Prenesti, E.; Stefano, C. D.; Sammartano, S. Speciation of N-(Phosphonomethyl)glycine (glyphosate) in Aqueous Solutions Containing Major Components of Natural Fluids Chem. Speciation Bioavailability 1996, 8, 59-65 10.1080/09542299.1996.11083270
14. Peixoto, M.; Bauerfeldt, G.; Herbst, M.; Pereira, M.; da Silva, C. Study of the Stepwise Deprotonation Reactions of Glyphosate and the Corresponding Pka Values in Aqueous Solution J. Phys. Chem. A 2015, 119, 5241-5249 10.1021/jp5099552
15. Sheals, J.; Persson, P.; Hedman, B. IR and EXAFS Spectroscopic Studies of Glyphosate Protonation and Copper(II) Complexes of Glyphosate in Aqueous Solution Inorg. Chem. 2001, 40, 4302-4309 10.1021/ic000849g
16. Barja, B. C.; Dos Santos Afonso, M. An AtR-FTIR Study of Glyphosate and Its Fe(III) Complex in Aqueous Solution Environ. Sci. Technol. 1998, 32, 3331-3335 10.1021/es9800380
17. 31P NMR and Zn EXAFS Study Environ. Sci. Technol. 2013, 47, 4211-4219 10.1021/es305120x
18. Motekaitis, R.; Martell, A. Metal Chelate Formation by N-Phosphonometylglycine and Related Ligands J. Coord. Chem. 1985, 14, 139-149 10.1080/00958978508073900
19. 2, and Related Ligands and of Their Complexes with Platinum(II) Inorg. Chem. 1986, 25, 726-734 10.1021/ic00226a005
20. Piccolo, A.; Celano, G. Modification of Infrared Spectra of the Herbicide Glyphosate Induced by pH Variation J. Environ. Sci. Health, Part B 1993, 28, 447-457 10.1080/03601239309372835
21. 13C NMR of Glyphosate: Comparison of pH Titrations to the Herbicidal Dead-End Complex with 5-Enolpyruvoylshikimate-3-Phosphate Synthase Biochemistry 1989, 28, 3856-3868 10.1021/bi00435a035
22. Morillo, E.; Undabeytia, T.; Maqueda, C. Adsorption of Glyphosate on the Clay Mineral Montmorillonite: Effect of Cu(II) in Solution and Adsorbed on the Mineral Environ. Sci. Technol. 1997, 31, 3588-3592 10.1021/es970341l
23. Mazzei, P.; Piccolo, A. Quantitative Evaluation of Noncovalent Interactions between Glyphosate and Dissolved Humic Substances by NMR Spectroscopy Environ. Sci. Technol. 2012, 46, 5939-5946 10.1021/es300265a
24. Tribe, L.; Kwon, K. D.; Trout, C. C.; Kubicki, J. D. Molecular Orbital Theory Study on Surface Complex Structures of Glyphosate on Goethite: Calculation of Vibrational Frequencies Environ. Sci. Technol. 2006, 40, 3836-3841 10.1021/es052363a
25. Undabeytia, T.; Morillo, E.; Maqueda, C. Ftir Study of Glyphosate-Copper Complexes J. Agric. Food Chem. 2002, 50, 1918-1921 10.1021/jf010988w
26. Piccolo, A.; Celano, G. Hydrogen-Bonding Interactions between the Herbicide Glyphosate and Water-Soluble Humic Substances Environ. Toxicol. Chem. 1994, 13, 1737-1741 10.1002/etc.5620131104
27. Gran, G. Determination of the Equivalence Point in Potentiometric Titrations. Part II Analyst 1952, 77, 661-671 10.1039/an9527700661
28. Li, X.; Zhang, Z.; Endrizzi, F.; Martin, L. R.; Luo, S.; Rao, L. Effect of Temperature on the Protonation of N-(2-Hydroxyethyl)Ethylenediamine-N,N′,N′-Triacetic Acid in Aqueous Solutions: Potentiometric and Calorimetric Studies J. Chem. Thermodyn. 2015, 85, 35-41 10.1016/j.jct.2014.12.026
29. Glasoe, P.; Long, F. Use of Glass Electrodes to Measure Acidities in Deuterium Oxide J. Phys. Chem. 1960, 64, 188-190 10.1021/j100830a521
30. Sheals, J.; Granström, M.; Sjöberg, S.; Persson, P. Coadsorption of Cu(II) and Glyphosate at the Water-Goethite (α-FeOOH) Interface: Molecular Structures from FTIR and EXAFS Measurements J. Colloid Interface Sci. 2003, 262, 38-47 10.1016/S0021-9797(03)00207-8
31. Wauchope, D. Acid Dissociation Constants of Arsenic Acid, Methylarsonic Acid (MAA), Dimethylarsinic Acid (Cacodylic Acid), and N-(Phosphonomethyl)Glycine (Glyphosate) J. Agric. Food Chem. 1976, 24, 717-721 10.1021/jf60206a010
32. Kobyłecka, J.; Ptaszyński, B.; Zwolinńska, A. Synthesis and Properties of Complexes of Lead(II), Cadmium(II), and Zinc(II) with N-Phosphonomethylglycine Monatsh. Chem. 2000, 131, 0001-0011 10.1007/s007060050001
33. Knuuttila, P.; Knuuttila, H. The Crystal and Molecular Structure of N-(Phosphonomethyl)glycine (Glyphosate) Acta Chem. Scand. 1979, 33b, 623-626 10.3891/acta.chem.scand.33b-0623
34. Tian, G.; Teat, S. J.; Zhang, Z.; Rao, L. Sequestering Uranium from Seawater: Binding Strength and Modes of Uranyl Complexes with Glutarimidedioxime Dalton Trans. 2012, 41, 11579-11586 10.1039/c2dt30978e
35. Li, W.; Feng, X.; Yan, Y.; Sparks, D.; Phillips, B. Solid-State NMR Spectroscopic Study of Phosphate Sorption Mechanisms on Aluminum (Hydr)Oxides Environ. Sci. Technol. 2013, 47, 8308-8315 10.1021/es400874s
36. 31H NMR Spectroscopy Forensic Sci. Int. 2004, 143 (2-3) 141-145 10.1016/j.forsciint.2004.03.025
37. Lipok, J.; Owsiak, T.; Młynarz, P.; Forlani, G.; Kafarski, P. Phosphorus NMR as a Tool to Study Mineralization of Organophosphonates-the Ability of Spirulina Spp. To Degrade Glyphosate Enzyme Microb. Technol. 2007, 41, 286-291 10.1016/j.enzmictec.2007.02.004
38. Ge, X.; d'Avignon, D.; Ackerman, J.; Sammons, R. Rapid Vacuolar Sequestration: The Horseweed Glyphosate Resistance Mechanism Pest Manage. Sci. 2010, 66, 345-348 10.1002/ps.1911
39. Johnson, E. C. The Interaction of Glyphosate with Soil Constituents. M.S. Dissertation, Purdue University: West Lafayette, IN, 2009.
40. Kudzin, Z.; Gralak, D.; Drabowicz, J.; Łuczak, J. Novel Approach for the Simultaneous Analysis of Glyphosate and Its Metabolites J. Chromatogr. A 2002, 947, 129-141 10.1016/S0021-9673(01)01603-X
41. Sheals, J.; Sjöberg, S.; Persson, P. Adsorption of Glyphosate on Goethite: Molecular Characterization of Surface Complexes Environ. Sci. Technol. 2002, 36, 3090-3095 10.1021/es010295w