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Effect of nitro substituent on electrochemical oxidation of phenols at boron-doped diamond anodes.
Chemosphere. 2010 Feb; 78(9):1093-9.C

Abstract

In order to investigate nitro-substitutent's effect on degradation of phenols at boron-doped diamond (BDD) anodes, cyclic voltammetries of three nitrophenol isomers: 2-nitrophenol (2NP), 3-nitrophenol (3NP) and 4-nitrophenol (4NP) were studied, and their bulk electrolysis results were compared with phenol's (Ph) under alkaline condition. The voltammetric study showed nitrophenols could be attacked by hydroxyl radicals and nitro-group was released from the aromatic ring. Results of bulk electrolysis showed degradation of all phenols were fit to a pseudo first-order equation and followed in this order: 2NP>4NP>3NP>Ph. Molecular structures, especially carbon atom charge, significantly influenced the electrochemical oxidation of these isomers. Intermediates were analyzed during the electrolysis process, and were mainly catechol, resorcinol, hydroquinone, and carboxylic acids, such as acetic acid and oxalic acid. A simple degradation pathway was proposed. Moreover, a linear increasing relationship between degradation rates and Hammett constants of the studied phenols was observed, which demonstrated that electrochemical oxidation of these phenols was mainly initiated by electrophilic attack of hydroxyl radicals at BDD anodes.

Authors+Show Affiliations

Department of Environmental Engineering, Peking University, The Key Laboratory of Water and Sediment Sciences, Ministry of Education, Beijing, China.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20060999

Citation

Jiang, Yi, et al. "Effect of Nitro Substituent On Electrochemical Oxidation of Phenols at Boron-doped Diamond Anodes." Chemosphere, vol. 78, no. 9, 2010, pp. 1093-9.
Jiang Y, Zhu X, Li H, et al. Effect of nitro substituent on electrochemical oxidation of phenols at boron-doped diamond anodes. Chemosphere. 2010;78(9):1093-9.
Jiang, Y., Zhu, X., Li, H., & Ni, J. (2010). Effect of nitro substituent on electrochemical oxidation of phenols at boron-doped diamond anodes. Chemosphere, 78(9), 1093-9. https://doi.org/10.1016/j.chemosphere.2009.12.036
Jiang Y, et al. Effect of Nitro Substituent On Electrochemical Oxidation of Phenols at Boron-doped Diamond Anodes. Chemosphere. 2010;78(9):1093-9. PubMed PMID: 20060999.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Effect of nitro substituent on electrochemical oxidation of phenols at boron-doped diamond anodes. AU - Jiang,Yi, AU - Zhu,Xiuping, AU - Li,Hongna, AU - Ni,Jinren, Y1 - 2010/01/12/ PY - 2009/11/13/received PY - 2009/12/16/revised PY - 2009/12/16/accepted PY - 2010/1/12/entrez PY - 2010/1/12/pubmed PY - 2010/5/5/medline SP - 1093 EP - 9 JF - Chemosphere JO - Chemosphere VL - 78 IS - 9 N2 - In order to investigate nitro-substitutent's effect on degradation of phenols at boron-doped diamond (BDD) anodes, cyclic voltammetries of three nitrophenol isomers: 2-nitrophenol (2NP), 3-nitrophenol (3NP) and 4-nitrophenol (4NP) were studied, and their bulk electrolysis results were compared with phenol's (Ph) under alkaline condition. The voltammetric study showed nitrophenols could be attacked by hydroxyl radicals and nitro-group was released from the aromatic ring. Results of bulk electrolysis showed degradation of all phenols were fit to a pseudo first-order equation and followed in this order: 2NP>4NP>3NP>Ph. Molecular structures, especially carbon atom charge, significantly influenced the electrochemical oxidation of these isomers. Intermediates were analyzed during the electrolysis process, and were mainly catechol, resorcinol, hydroquinone, and carboxylic acids, such as acetic acid and oxalic acid. A simple degradation pathway was proposed. Moreover, a linear increasing relationship between degradation rates and Hammett constants of the studied phenols was observed, which demonstrated that electrochemical oxidation of these phenols was mainly initiated by electrophilic attack of hydroxyl radicals at BDD anodes. SN - 1879-1298 UR - https://www.unboundmedicine.com/medline/citation/20060999/Effect_of_nitro_substituent_on_electrochemical_oxidation_of_phenols_at_boron_doped_diamond_anodes_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0045-6535(09)01459-3 DB - PRIME DP - Unbound Medicine ER -