Probing and Comparing the Photobromination and Photoiodination of Dissolved Organic Matter by Using Ultra-High-Resolution Mass Spectrometry

Photochemical halogenation of dissolved organic matter (DOM) may represent an important abiotic process for the formation of natural organobromine compounds (OBCs) and natural organoiodine compounds (OICs) within surface waters. Here we report the enhanced formation of OBCs and OICs by photohalogena...

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Veröffentlicht in:Environmental science & technology 2017-05, Vol.51 (10), p.5464-5472
Hauptverfasser: Hao, Zhineng, Yin, Yongguang, Cao, Dong, Liu, Jingfu
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Yin, Yongguang
Cao, Dong
Liu, Jingfu
description Photochemical halogenation of dissolved organic matter (DOM) may represent an important abiotic process for the formation of natural organobromine compounds (OBCs) and natural organoiodine compounds (OICs) within surface waters. Here we report the enhanced formation of OBCs and OICs by photohalogenating DOM in freshwater and seawater, as well as the noticeable difference in the distribution and composition pattern of newly formed OBCs and OICs. By using negative ion electrospray ionization coupled with Fourier transform ion cyclotron resonance mass spectrometry, various OBCs and OICs were identified during the photohalogenation processes in sunlit waters. The respective number of OBCs and OICs formed in artificial seawater (ASW) under light radiation was higher than that in artificial freshwater (AFW), suggesting a possible role of the mixed reactive halogen species. OBCs were formed mainly via substitution reactions and addition reactions accompanied by other reactions and distributed into three classes: unsaturated hydrocarbons with relatively low oxygen content, unsaturated aliphatic compounds, and saturated fatty acids and carbohydrates with relatively high hydrogen content. Unlike the OBCs, OICs were located primarily in the region of carboxylic-rich alicyclic molecules composed of esterified phenolic, carboxylated, and fused alicyclic structures and were generated mainly through electrophilic substitution of the aromatic proton. Our findings call for further investigation on the exact structure and toxicity of the OBCs and OICs generated in the natural environment.
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Sci. Technol</addtitle><description>Photochemical halogenation of dissolved organic matter (DOM) may represent an important abiotic process for the formation of natural organobromine compounds (OBCs) and natural organoiodine compounds (OICs) within surface waters. Here we report the enhanced formation of OBCs and OICs by photohalogenating DOM in freshwater and seawater, as well as the noticeable difference in the distribution and composition pattern of newly formed OBCs and OICs. By using negative ion electrospray ionization coupled with Fourier transform ion cyclotron resonance mass spectrometry, various OBCs and OICs were identified during the photohalogenation processes in sunlit waters. The respective number of OBCs and OICs formed in artificial seawater (ASW) under light radiation was higher than that in artificial freshwater (AFW), suggesting a possible role of the mixed reactive halogen species. 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subjects Aliphatic compounds
Artificial seawater
Bromine Compounds - chemistry
Carbohydrates
Chemical analysis
Comparative analysis
Cyclotron resonance
Dissolved organic matter
Esterification
Fatty acids
Fourier transforms
Fresh Water
Halogenation
High resolution
Hydrocarbons
Iodine Compounds - chemistry
Ionization
Ions
Mass Spectrometry
Mass spectroscopy
Molecules
Organobromine compounds
Oxygen content
Phenolic compounds
Phenols
Radiation
Saturated hydrocarbons
Scientific imaging
Seawater
Seawater - chemistry
Spectrometry, Mass, Electrospray Ionization
Spectroscopy
Substitution reactions
Surface water
Toxicity
Unsaturated hydrocarbons
Water analysis
title Probing and Comparing the Photobromination and Photoiodination of Dissolved Organic Matter by Using Ultra-High-Resolution Mass Spectrometry
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