Thermodynamic Study on the Protonation Reactions of Glyphosate in Aqueous Solution: Potentiometry, Calorimetry and NMR spectroscopy
Glyphosate [N-(phosphonomethyl)glycine] has been described as the ideal herbicide because of its unique properties. There is some conflicting information concerning the structures and conformations involved in the protonation process of glyphosate. Protonation may influence the chemical and physica...
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| Published in | The journal of physical chemistry. B Vol. 120; no. 9; pp. 2132 - 2137 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
10.03.2016
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| Subjects | |
| Online Access | Get full text |
| ISSN | 1520-6106 1520-5207 1520-5207 |
| DOI | 10.1021/acs.jpcb.5b11550 |
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| Abstract | Glyphosate [N-(phosphonomethyl)glycine] has been described as the ideal herbicide because of its unique properties. There is some conflicting information concerning the structures and conformations involved in the protonation process of glyphosate. Protonation may influence the chemical and physical properties of glyphosate, modifying its structure and the chemical processes in which it is involved. To better understand the species in solution associated with changes in pH, thermodynamic study (potentiometry, calorimetry and NMR spectroscopy) about the protonation pathway of glyphosate is performed. Experimental results confirmed that the order of successive protonation sites of totally deprotonated glyphosate is phosphonate oxygen, amino nitrogen, and finally carboxylate oxygen. This trend is in agreement with the most recent theoretical work in the literature on the subject ( J. Phys. Chem. A 2015, 119, 5241−5249 ). The result is important because it confirms that the protonated site of glyphosate in pH range 7–8, is not on the amino but on the phosphonate group instead. This corrected information can improve the understanding of the glyphosate chemical and biochemical action. |
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| AbstractList | Glyphosate [N-(phosphonomethyl)glycine] has been described as the ideal herbicide because of its unique properties. There is some conflicting information concerning the structures and conformations involved in the protonation process of glyphosate. Protonation may influence the chemical and physical properties of glyphosate, modifying its structure and the chemical processes in which it is involved. To better understand the species in solution associated with changes in pH, thermodynamic study (potentiometry, calorimetry and NMR spectroscopy) about the protonation pathway of glyphosate is performed. Experimental results confirmed that the order of successive protonation sites of totally deprotonated glyphosate is phosphonate oxygen, amino nitrogen, and finally carboxylate oxygen. This trend is in agreement with the most recent theoretical work in the literature on the subject (J. Phys. Chem. A 2015,, 119, 5241−5249). The result is important because it confirms that the protonated site of glyphosate in pH range 7–8, is not on the amino but on the phosphonate group instead. This corrected information can improve the understanding of the glyphosate chemical and biochemical action. Glyphosate [N-(phosphonomethyl)glycine] has been described as the ideal herbicide because of its unique properties. There is some conflicting information concerning the structures and conformations involved in the protonation process of glyphosate. Protonation may influence the chemical and physical properties of glyphosate, modifying its structure and the chemical processes in which it is involved. To better understand the species in solution associated with changes in pH, thermodynamic study (potentiometry, calorimetry and NMR spectroscopy) about the protonation pathway of glyphosate is performed. Experimental results confirmed that the order of successive protonation sites of totally deprotonated glyphosate is phosphonate oxygen, amino nitrogen, and finally carboxylate oxygen. This trend is in agreement with the most recent theoretical work in the literature on the subject (J. Phys. Chem. A 2015, 119, 5241-5249). The result is important because it confirms that the protonated site of glyphosate in pH range 7-8, is not on the amino but on the phosphonate group instead. This corrected information can improve the understanding of the glyphosate chemical and biochemical action.Glyphosate [N-(phosphonomethyl)glycine] has been described as the ideal herbicide because of its unique properties. There is some conflicting information concerning the structures and conformations involved in the protonation process of glyphosate. Protonation may influence the chemical and physical properties of glyphosate, modifying its structure and the chemical processes in which it is involved. To better understand the species in solution associated with changes in pH, thermodynamic study (potentiometry, calorimetry and NMR spectroscopy) about the protonation pathway of glyphosate is performed. Experimental results confirmed that the order of successive protonation sites of totally deprotonated glyphosate is phosphonate oxygen, amino nitrogen, and finally carboxylate oxygen. This trend is in agreement with the most recent theoretical work in the literature on the subject (J. Phys. Chem. A 2015, 119, 5241-5249). The result is important because it confirms that the protonated site of glyphosate in pH range 7-8, is not on the amino but on the phosphonate group instead. This corrected information can improve the understanding of the glyphosate chemical and biochemical action. Glyphosate [N-(phosphonomethyl)glycine] has been described as the ideal herbicide because of its unique properties. There is some conflicting information concerning the structures and conformations involved in the protonation process of glyphosate. Protonation may influence the chemical and physical properties of glyphosate, modifying its structure and the chemical processes in which it is involved. To better understand the species in solution associated with changes in pH, thermodynamic study (potentiometry, calorimetry and NMR spectroscopy) about the protonation pathway of glyphosate is performed. Experimental results confirmed that the order of successive protonation sites of totally deprotonated glyphosate is phosphonate oxygen, amino nitrogen, and finally carboxylate oxygen. This trend is in agreement with the most recent theoretical work in the literature on the subject (J. Phys. Chem. A 2015, 119, 5241-5249). The result is important because it confirms that the protonated site of glyphosate in pH range 7-8, is not on the amino but on the phosphonate group instead. This corrected information can improve the understanding of the glyphosate chemical and biochemical action. Glyphosate [N-(phosphonomethyl)glycine] has been described as the ideal herbicide because of its unique properties. There is some conflicting information concerning the structures and conformations involved in the protonation process of glyphosate. Protonation may influence the chemical and physical properties of glyphosate, modifying its structure and the chemical processes in which it is involved. To better understand the species in solution associated with changes in pH, thermodynamic study (potentiometry, calorimetry and NMR spectroscopy) about the protonation pathway of glyphosate is performed. Experimental results confirmed that the order of successive protonation sites of totally deprotonated glyphosate is phosphonate oxygen, amino nitrogen, and finally carboxylate oxygen. This trend is in agreement with the most recent theoretical work in the literature on the subject ( J. Phys. Chem. A 2015, 119, 5241−5249 ). The result is important because it confirms that the protonated site of glyphosate in pH range 7–8, is not on the amino but on the phosphonate group instead. This corrected information can improve the understanding of the glyphosate chemical and biochemical action. |
| Author | Li, Xingliang Liu, Bijun Dong, Lan Yu, Qianhong Wu, Fengchang Tan, Zhaoyi Luo, Shunzhong |
| AuthorAffiliation | Institute of Nuclear Physics and Chemistry Chinese Research Academy of Environmental Sciences China Academy of Engineering Physics State Key Laboratory of Environmental Criteria and Risk Assessment |
| AuthorAffiliation_xml | – name: Institute of Nuclear Physics and Chemistry – name: State Key Laboratory of Environmental Criteria and Risk Assessment – name: China Academy of Engineering Physics – name: Chinese Research Academy of Environmental Sciences |
| Author_xml | – sequence: 1 givenname: Bijun surname: Liu fullname: Liu, Bijun – sequence: 2 givenname: Lan surname: Dong fullname: Dong, Lan – sequence: 3 givenname: Qianhong surname: Yu fullname: Yu, Qianhong – sequence: 4 givenname: Xingliang surname: Li fullname: Li, Xingliang email: xingliang@caep.cn – sequence: 5 givenname: Fengchang surname: Wu fullname: Wu, Fengchang email: wufengchang@vip.skleg.cn – sequence: 6 givenname: Zhaoyi surname: Tan fullname: Tan, Zhaoyi – sequence: 7 givenname: Shunzhong surname: Luo fullname: Luo, Shunzhong email: luoshzh@caep.cn |
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| Snippet | Glyphosate [N-(phosphonomethyl)glycine] has been described as the ideal herbicide because of its unique properties. There is some conflicting information... Glyphosate [N-(phosphonomethyl)glycine] has been described as the ideal herbicide because of its unique properties. There is some conflicting information... |
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| SubjectTerms | amino nitrogen aqueous solutions Calorimetry Calorimetry - methods Electrical measurements Glycine - analogs & derivatives Glycine - chemistry Glyphosate Herbicides - chemistry Magnetic Resonance Spectroscopy - methods NMR spectroscopy nuclear magnetic resonance spectroscopy Oxygen Phosphonates physical chemistry physical properties Potentiometry - methods Protonation Protons Solutions - chemistry Thermodynamics Water - chemistry |
| Title | Thermodynamic Study on the Protonation Reactions of Glyphosate in Aqueous Solution: Potentiometry, Calorimetry and NMR spectroscopy |
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