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Oxidation of Sulfonamide Antibiotics of Six-Membered Heterocyclic Moiety by Ferrate(VI): Kinetics and Mechanistic Insight into SO2 Extrusion.
Environ Sci Technol. 2019 03 05; 53(5):2695-2704.ES

Abstract

This work presents ferrate(VI) (FeVIO42-, FeVI) oxidation of a wide range of sulfonamide antibiotics (SAs) containing five- and six-membered heterocyclic moieties (R) in their molecular structures. Kinetics measurements of the reactions between FeVI and SAs at different pH (6.5-10.0) give species-specific second-order rate constants, k5 and k6 of the reactions of protonated FeVI (HFeO4-) and unprotonated FeVI (FeVIO42-) with protonated SAs (HX), respectively. The values of k5 varied from (1.2 ± 0.1) × 103 to (2.2 ± 0.2) × 104 M-1 s-1, while the range of k6 was from (1.1 ± 0.1) × 102 to (1.0 ± 0.1) × 103 M-1 s-1 for different SAs. The transformation products of reaction between FeVI and sulfadiazine (SDZ, contains a six-membered R) include SO2 extrusion oxidized products (OPs) and aniline hydroxylated products. Comparatively, oxidation of sulfisoxazole (SIZ, a five-membered R) by FeVI has OPs that have no SO2 extrusion in their structures. Density functional theory calculations are performed to demonstrate SO2 extrusion in oxidation of SDZ by FeVI. The detailed mechanisms of oxidation are proposed to describe the differences in the oxidation of six- and five-membered heterocyclic moieties (R) containing SAs (i.e., SDZ versus SIZ) by FeVI.

Authors+Show Affiliations

Department of Environmental and Occupational Health, School of Public Health , Texas A&M University , College Station , Texas 77843 , United States.Department of Biomedical and Chemical Engineering and Sciences , Florida Institute of Technology , Melbourne , Florida 32901 , United States.Department of Biomedical and Chemical Engineering and Sciences , Florida Institute of Technology , Melbourne , Florida 32901 , United States.School of Earth Sciences and Environmental Engineering , Gwangju Institute of Science and Technology (GIST) , Gwangju 61005 , Republic of Korea.School of Civil and Environmental Engineering , Georgia Institute of Technology , Atlanta , Georgia 30332 , United States.Department of Environmental and Occupational Health, School of Public Health , Texas A&M University , College Station , Texas 77843 , United States.

Pub Type(s)

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

Language

eng

PubMed ID

30715861

Citation

Feng, Mingbao, et al. "Oxidation of Sulfonamide Antibiotics of Six-Membered Heterocyclic Moiety By Ferrate(VI): Kinetics and Mechanistic Insight Into SO2 Extrusion." Environmental Science & Technology, vol. 53, no. 5, 2019, pp. 2695-2704.
Feng M, Baum JC, Nesnas N, et al. Oxidation of Sulfonamide Antibiotics of Six-Membered Heterocyclic Moiety by Ferrate(VI): Kinetics and Mechanistic Insight into SO2 Extrusion. Environ Sci Technol. 2019;53(5):2695-2704.
Feng, M., Baum, J. C., Nesnas, N., Lee, Y., Huang, C. H., & Sharma, V. K. (2019). Oxidation of Sulfonamide Antibiotics of Six-Membered Heterocyclic Moiety by Ferrate(VI): Kinetics and Mechanistic Insight into SO2 Extrusion. Environmental Science & Technology, 53(5), 2695-2704. https://doi.org/10.1021/acs.est.8b06535
Feng M, et al. Oxidation of Sulfonamide Antibiotics of Six-Membered Heterocyclic Moiety By Ferrate(VI): Kinetics and Mechanistic Insight Into SO2 Extrusion. Environ Sci Technol. 2019 03 5;53(5):2695-2704. PubMed PMID: 30715861.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Oxidation of Sulfonamide Antibiotics of Six-Membered Heterocyclic Moiety by Ferrate(VI): Kinetics and Mechanistic Insight into SO2 Extrusion. AU - Feng,Mingbao, AU - Baum,J Clayton, AU - Nesnas,Nasri, AU - Lee,Yunho, AU - Huang,Ching-Hua, AU - Sharma,Virender K, Y1 - 2019/02/15/ PY - 2019/2/5/pubmed PY - 2019/9/19/medline PY - 2019/2/5/entrez SP - 2695 EP - 2704 JF - Environmental science & technology JO - Environ Sci Technol VL - 53 IS - 5 N2 - This work presents ferrate(VI) (FeVIO42-, FeVI) oxidation of a wide range of sulfonamide antibiotics (SAs) containing five- and six-membered heterocyclic moieties (R) in their molecular structures. Kinetics measurements of the reactions between FeVI and SAs at different pH (6.5-10.0) give species-specific second-order rate constants, k5 and k6 of the reactions of protonated FeVI (HFeO4-) and unprotonated FeVI (FeVIO42-) with protonated SAs (HX), respectively. The values of k5 varied from (1.2 ± 0.1) × 103 to (2.2 ± 0.2) × 104 M-1 s-1, while the range of k6 was from (1.1 ± 0.1) × 102 to (1.0 ± 0.1) × 103 M-1 s-1 for different SAs. The transformation products of reaction between FeVI and sulfadiazine (SDZ, contains a six-membered R) include SO2 extrusion oxidized products (OPs) and aniline hydroxylated products. Comparatively, oxidation of sulfisoxazole (SIZ, a five-membered R) by FeVI has OPs that have no SO2 extrusion in their structures. Density functional theory calculations are performed to demonstrate SO2 extrusion in oxidation of SDZ by FeVI. The detailed mechanisms of oxidation are proposed to describe the differences in the oxidation of six- and five-membered heterocyclic moieties (R) containing SAs (i.e., SDZ versus SIZ) by FeVI. SN - 1520-5851 UR - https://www.unboundmedicine.com/medline/citation/30715861/Oxidation_of_Sulfonamide_Antibiotics_of_Six_Membered_Heterocyclic_Moiety_by_Ferrate_VI_:_Kinetics_and_Mechanistic_Insight_into_SO2_Extrusion_ L2 - https://doi.org/10.1021/acs.est.8b06535 DB - PRIME DP - Unbound Medicine ER -