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ABTS as an Electron Shuttle to Enhance the Oxidation Kinetics of Substituted Phenols by Aqueous Permanganate.
Environ Sci Technol. 2015 Oct 06; 49(19):11764-71.ES

Abstract

In this study, it was, interestingly, found that 2,2'-azino-bis(3-ethylbenzothiazoline)-6-sulfonate (ABTS), a widely used electron shuttle, could greatly accelerate the oxidation of substituted phenols by potassium permanganate (Mn(VII)) in aqueous solutions at pH 5-9. This was attributed to the fact that these substituted phenols could be readily oxidized by the stable radical cation (ABTS(•+)), which was quickly produced from the oxidation of ABTS by Mn(VII). The reaction of Mn(VII) with ABTS exhibited second-order kinetics, with stoichiometries of ∼5:1 at pH 5-6 and ∼3:1 at pH 7-9, and the rate constants varied negligibly from pH 5 to 9 (k = (9.44 ± 0.21) × 10(4) M(-1) s(-1)). Comparatively, the reaction of ABTS(•+) with phenol showed biphasic kinetics. The second-order rate constants for the reactions of ABTS(•+) with substituted phenols obtained in the initial phase were strongly affected by pH, and they were several orders of magnitude higher than those for the reactions of Mn(VII) with substituted phenols at each pH. Good Hammett-type correlations were found for the reactions of ABTS(•+) with undissociated (log(k) = 2.82-4.31σ) and dissociated phenols (log(k) = 7.29-5.90σ). The stoichiometries of (2.2 ± 0.06):1 (ABTS(•+) in excess) and (1.38 ± 0.18):1 (phenol in excess) were achieved in the reaction of ABTS(•+) with phenol, but they exhibited no pH dependency.

Authors+Show Affiliations

State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology , Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology , Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology , Harbin 150090, China.Key Laboratory of Green Chemical Engineering and Technology of College of Heilongjiang Province, College of Chemical and Environmental Engineering, Harbin University of Science and Technology , Harbin 150040, China.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology , Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology , Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology , Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology , Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology , Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology , Harbin 150090, China.

Pub Type(s)

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

Language

eng

PubMed ID

26378975

Citation

Song, Yang, et al. "ABTS as an Electron Shuttle to Enhance the Oxidation Kinetics of Substituted Phenols By Aqueous Permanganate." Environmental Science & Technology, vol. 49, no. 19, 2015, pp. 11764-71.
Song Y, Jiang J, Ma J, et al. ABTS as an Electron Shuttle to Enhance the Oxidation Kinetics of Substituted Phenols by Aqueous Permanganate. Environ Sci Technol. 2015;49(19):11764-71.
Song, Y., Jiang, J., Ma, J., Pang, S. Y., Liu, Y. Z., Yang, Y., Luo, C. W., Zhang, J. Q., Gu, J., & Qin, W. (2015). ABTS as an Electron Shuttle to Enhance the Oxidation Kinetics of Substituted Phenols by Aqueous Permanganate. Environmental Science & Technology, 49(19), 11764-71. https://doi.org/10.1021/acs.est.5b03358
Song Y, et al. ABTS as an Electron Shuttle to Enhance the Oxidation Kinetics of Substituted Phenols By Aqueous Permanganate. Environ Sci Technol. 2015 Oct 6;49(19):11764-71. PubMed PMID: 26378975.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - ABTS as an Electron Shuttle to Enhance the Oxidation Kinetics of Substituted Phenols by Aqueous Permanganate. AU - Song,Yang, AU - Jiang,Jin, AU - Ma,Jun, AU - Pang,Su-Yan, AU - Liu,Yong-Ze, AU - Yang,Yi, AU - Luo,Cong-Wei, AU - Zhang,Jian-Qiao, AU - Gu,Jia, AU - Qin,Wen, Y1 - 2015/09/28/ PY - 2015/9/18/entrez PY - 2015/9/18/pubmed PY - 2016/5/15/medline SP - 11764 EP - 71 JF - Environmental science & technology JO - Environ Sci Technol VL - 49 IS - 19 N2 - In this study, it was, interestingly, found that 2,2'-azino-bis(3-ethylbenzothiazoline)-6-sulfonate (ABTS), a widely used electron shuttle, could greatly accelerate the oxidation of substituted phenols by potassium permanganate (Mn(VII)) in aqueous solutions at pH 5-9. This was attributed to the fact that these substituted phenols could be readily oxidized by the stable radical cation (ABTS(•+)), which was quickly produced from the oxidation of ABTS by Mn(VII). The reaction of Mn(VII) with ABTS exhibited second-order kinetics, with stoichiometries of ∼5:1 at pH 5-6 and ∼3:1 at pH 7-9, and the rate constants varied negligibly from pH 5 to 9 (k = (9.44 ± 0.21) × 10(4) M(-1) s(-1)). Comparatively, the reaction of ABTS(•+) with phenol showed biphasic kinetics. The second-order rate constants for the reactions of ABTS(•+) with substituted phenols obtained in the initial phase were strongly affected by pH, and they were several orders of magnitude higher than those for the reactions of Mn(VII) with substituted phenols at each pH. Good Hammett-type correlations were found for the reactions of ABTS(•+) with undissociated (log(k) = 2.82-4.31σ) and dissociated phenols (log(k) = 7.29-5.90σ). The stoichiometries of (2.2 ± 0.06):1 (ABTS(•+) in excess) and (1.38 ± 0.18):1 (phenol in excess) were achieved in the reaction of ABTS(•+) with phenol, but they exhibited no pH dependency. SN - 1520-5851 UR - https://www.unboundmedicine.com/medline/citation/26378975/ABTS_as_an_Electron_Shuttle_to_Enhance_the_Oxidation_Kinetics_of_Substituted_Phenols_by_Aqueous_Permanganate_ L2 - https://doi.org/10.1021/acs.est.5b03358 DB - PRIME DP - Unbound Medicine ER -