1. Thermodynamic Study on the Protonation Reactions of Glyphosate in Aqueous Solution: Potentiometry, Calorimetry and NMR spectroscopy
- Author
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Fengchang Wu, Zhaoyi Tan, Xingliang Li, Lan Dong, Bijun Liu, Qianhong Yu, and Shunzhong Luo
- Subjects
Magnetic Resonance Spectroscopy ,Glycine ,Protonation ,Calorimetry ,010501 environmental sciences ,010402 general chemistry ,01 natural sciences ,chemistry.chemical_compound ,Deprotonation ,Computational chemistry ,Materials Chemistry ,Organic chemistry ,Carboxylate ,Physical and Theoretical Chemistry ,0105 earth and related environmental sciences ,Aqueous solution ,Herbicides ,Water ,Nuclear magnetic resonance spectroscopy ,Phosphonate ,0104 chemical sciences ,Surfaces, Coatings and Films ,Solutions ,chemistry ,Potentiometry ,Thermodynamics ,Protons - 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.
- Published
- 2016
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