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 |
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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. |
doi_str_mv | 10.1021/acs.est.6b03887 |
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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.</description><identifier>ISSN: 0013-936X</identifier><identifier>EISSN: 1520-5851</identifier><identifier>DOI: 10.1021/acs.est.6b03887</identifier><identifier>PMID: 28440636</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>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</subject><ispartof>Environmental science & technology, 2017-05, Vol.51 (10), p.5464-5472</ispartof><rights>Copyright © 2017 American Chemical Society</rights><rights>Copyright American Chemical Society May 16, 2017</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a514t-96b14fbebc7e8b56a6a747a2f1b9e57ea5fb0e64bdbba8ab06daf383bb41e1a43</citedby><cites>FETCH-LOGICAL-a514t-96b14fbebc7e8b56a6a747a2f1b9e57ea5fb0e64bdbba8ab06daf383bb41e1a43</cites><orcidid>0000-0001-8793-4401 ; 0000-0001-7134-7026</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.est.6b03887$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.est.6b03887$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27081,27929,27930,56743,56793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28440636$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hao, Zhineng</creatorcontrib><creatorcontrib>Yin, Yongguang</creatorcontrib><creatorcontrib>Cao, Dong</creatorcontrib><creatorcontrib>Liu, Jingfu</creatorcontrib><title>Probing and Comparing the Photobromination and Photoiodination of Dissolved Organic Matter by Using Ultra-High-Resolution Mass Spectrometry</title><title>Environmental science & technology</title><addtitle>Environ. 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. 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. 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Yin, Yongguang ; Cao, Dong ; Liu, Jingfu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a514t-96b14fbebc7e8b56a6a747a2f1b9e57ea5fb0e64bdbba8ab06daf383bb41e1a43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Aliphatic compounds</topic><topic>Artificial seawater</topic><topic>Bromine Compounds - chemistry</topic><topic>Carbohydrates</topic><topic>Chemical analysis</topic><topic>Comparative analysis</topic><topic>Cyclotron resonance</topic><topic>Dissolved organic matter</topic><topic>Esterification</topic><topic>Fatty acids</topic><topic>Fourier transforms</topic><topic>Fresh Water</topic><topic>Halogenation</topic><topic>High resolution</topic><topic>Hydrocarbons</topic><topic>Iodine Compounds - chemistry</topic><topic>Ionization</topic><topic>Ions</topic><topic>Mass Spectrometry</topic><topic>Mass spectroscopy</topic><topic>Molecules</topic><topic>Organobromine compounds</topic><topic>Oxygen content</topic><topic>Phenolic compounds</topic><topic>Phenols</topic><topic>Radiation</topic><topic>Saturated hydrocarbons</topic><topic>Scientific imaging</topic><topic>Seawater</topic><topic>Seawater - chemistry</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Spectroscopy</topic><topic>Substitution reactions</topic><topic>Surface water</topic><topic>Toxicity</topic><topic>Unsaturated hydrocarbons</topic><topic>Water analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hao, Zhineng</creatorcontrib><creatorcontrib>Yin, Yongguang</creatorcontrib><creatorcontrib>Cao, Dong</creatorcontrib><creatorcontrib>Liu, Jingfu</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Environment Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Environment Abstracts</collection><jtitle>Environmental science & technology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hao, Zhineng</au><au>Yin, Yongguang</au><au>Cao, Dong</au><au>Liu, Jingfu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Probing and Comparing the Photobromination and Photoiodination of Dissolved Organic Matter by Using Ultra-High-Resolution Mass Spectrometry</atitle><jtitle>Environmental science & technology</jtitle><addtitle>Environ. Sci. Technol</addtitle><date>2017-05-16</date><risdate>2017</risdate><volume>51</volume><issue>10</issue><spage>5464</spage><epage>5472</epage><pages>5464-5472</pages><issn>0013-936X</issn><eissn>1520-5851</eissn><abstract>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.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>28440636</pmid><doi>10.1021/acs.est.6b03887</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-8793-4401</orcidid><orcidid>https://orcid.org/0000-0001-7134-7026</orcidid><oa>free_for_read</oa></addata></record> |
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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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