Ortho-hydroxyl effect and proton transfer via ion-neutral complex: the fragmentation study of protonated imine resveratrol analogues in mass spectrometry
The fragmentation pathways of protonated imine resveratrol analogues in the gas‐phase were investigated by electrospray ionization–tandem mass spectrometry. Benzyl cations were formed in the imine resveratrol analogues that had an ortho‐hydroxyl group on the benzene ring A. The specific elimination...
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| Veröffentlicht in: | Journal of mass spectrometry. 2016-07, Vol.51 (7), p.518-523 |
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| creator | Yue, Lei Li, Jing Xie, Xiaodong Guo, Cheng Yin, Xinchi Yin, Qi Chen, Yinjuan Pan, Yuanjiang Ding, Chuanfan |
| description | The fragmentation pathways of protonated imine resveratrol analogues in the gas‐phase were investigated by electrospray ionization–tandem mass spectrometry. Benzyl cations were formed in the imine resveratrol analogues that had an ortho‐hydroxyl group on the benzene ring A. The specific elimination of the quinomethane neutral, CH2 = C6H4 = O, from the two isomeric ions [M1 + H]+ and [M3 + H]+ via the corresponding ion–neutral complexes was observed. The fragmentation pathway for the related meta‐isomer, ion [M2 + H]+ and the other congeners was not observed. Accurate mass measurements and additional experiments carried out with a chlorinated analogue and the trideuterated isotopolog of M1 supported the overall interpretation of the fragmentation phenomena observed. It is very helpful for understanding the intriguing roles of ortho‐hydroxyl effect and ion–neutral complexes in fragmentation reactions and enriching the knowledge of the gas‐phase chemistry of the benzyl cation. Copyright © 2016 John Wiley & Sons, Ltd. |
| doi_str_mv | 10.1002/jms.3778 |
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Benzyl cations were formed in the imine resveratrol analogues that had an ortho‐hydroxyl group on the benzene ring A. The specific elimination of the quinomethane neutral, CH2 = C6H4 = O, from the two isomeric ions [M1 + H]+ and [M3 + H]+ via the corresponding ion–neutral complexes was observed. The fragmentation pathway for the related meta‐isomer, ion [M2 + H]+ and the other congeners was not observed. Accurate mass measurements and additional experiments carried out with a chlorinated analogue and the trideuterated isotopolog of M1 supported the overall interpretation of the fragmentation phenomena observed. It is very helpful for understanding the intriguing roles of ortho‐hydroxyl effect and ion–neutral complexes in fragmentation reactions and enriching the knowledge of the gas‐phase chemistry of the benzyl cation. Copyright © 2016 John Wiley & Sons, Ltd.</description><identifier>ISSN: 1076-5174</identifier><identifier>EISSN: 1096-9888</identifier><identifier>DOI: 10.1002/jms.3778</identifier><identifier>PMID: 27434810</identifier><language>eng</language><publisher>England: Blackwell Publishing Ltd</publisher><subject>benzyl cation ; Cations ; Chlorination ; Congeners ; Fragmentation ; imine resveratrol analogue ; Imines ; ion-neutral complex ; Mass spectrometry ; ortho-hydroxyl effect ; Pathways ; proton transfer ; Rings (mathematics)</subject><ispartof>Journal of mass spectrometry., 2016-07, Vol.51 (7), p.518-523</ispartof><rights>Copyright © 2016 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4908-a99f7dbcbb58442b11732e3ffa92aba5967893b324cb834f3afc5bdf09682c833</citedby><cites>FETCH-LOGICAL-c4908-a99f7dbcbb58442b11732e3ffa92aba5967893b324cb834f3afc5bdf09682c833</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjms.3778$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjms.3778$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27434810$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yue, Lei</creatorcontrib><creatorcontrib>Li, Jing</creatorcontrib><creatorcontrib>Xie, Xiaodong</creatorcontrib><creatorcontrib>Guo, Cheng</creatorcontrib><creatorcontrib>Yin, Xinchi</creatorcontrib><creatorcontrib>Yin, Qi</creatorcontrib><creatorcontrib>Chen, Yinjuan</creatorcontrib><creatorcontrib>Pan, Yuanjiang</creatorcontrib><creatorcontrib>Ding, Chuanfan</creatorcontrib><title>Ortho-hydroxyl effect and proton transfer via ion-neutral complex: the fragmentation study of protonated imine resveratrol analogues in mass spectrometry</title><title>Journal of mass spectrometry.</title><addtitle>J. Mass Spectrom</addtitle><description>The fragmentation pathways of protonated imine resveratrol analogues in the gas‐phase were investigated by electrospray ionization–tandem mass spectrometry. Benzyl cations were formed in the imine resveratrol analogues that had an ortho‐hydroxyl group on the benzene ring A. The specific elimination of the quinomethane neutral, CH2 = C6H4 = O, from the two isomeric ions [M1 + H]+ and [M3 + H]+ via the corresponding ion–neutral complexes was observed. The fragmentation pathway for the related meta‐isomer, ion [M2 + H]+ and the other congeners was not observed. Accurate mass measurements and additional experiments carried out with a chlorinated analogue and the trideuterated isotopolog of M1 supported the overall interpretation of the fragmentation phenomena observed. It is very helpful for understanding the intriguing roles of ortho‐hydroxyl effect and ion–neutral complexes in fragmentation reactions and enriching the knowledge of the gas‐phase chemistry of the benzyl cation. Copyright © 2016 John Wiley & Sons, Ltd.</description><subject>benzyl cation</subject><subject>Cations</subject><subject>Chlorination</subject><subject>Congeners</subject><subject>Fragmentation</subject><subject>imine resveratrol analogue</subject><subject>Imines</subject><subject>ion-neutral complex</subject><subject>Mass spectrometry</subject><subject>ortho-hydroxyl effect</subject><subject>Pathways</subject><subject>proton transfer</subject><subject>Rings (mathematics)</subject><issn>1076-5174</issn><issn>1096-9888</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqNkstu1DAUhiMEoqUg8QTIEhs2Kb7FF3ZQ0QIa2kVBs7Sc5LiTIYmntlMmj8Lb4qHDLJCQurJlffrOr-O_KF4SfEowpm_XQzxlUqpHxTHBWpRaKfV4d5eirIjkR8WzGNcYY625eFocUckZVwQfF7-uQlr5cjW3wW_nHoFz0CRkxxZtgk9-RCnYMToI6K6zqPNjOcKU33rU-GHTw_YdSitALtibAcZkU0ZQTFM7I-_2DpugRd3QjYACxDsINgXf5yG29zcTRNSNaLAxorjJw4MfIIX5efHE2T7Ci_15Unw___jt7FO5uLr4fPZ-UTZcY1VarZ1s66auK8U5rQmRjAJzzmpqa1tpIZVmNaO8qRXjjlnXVHXr8poUbRRjJ8Wbe2_OepvDJDN0sYG-tyP4KRqiWCUoZUI_AMVKcMywfAgqsJQVJhl9_Q-69lPIu_lDVVRimTMchE3wMQZwZhO6wYbZEGx2JTC5BGZXgoy-2guneoD2AP799QyU98DProf5vyLz5ev1Xrjnu5hge-Bt-GGEZLIyy8sLc_0Bi_PF5dIs2W8mCs07</recordid><startdate>201607</startdate><enddate>201607</enddate><creator>Yue, Lei</creator><creator>Li, Jing</creator><creator>Xie, Xiaodong</creator><creator>Guo, Cheng</creator><creator>Yin, Xinchi</creator><creator>Yin, Qi</creator><creator>Chen, Yinjuan</creator><creator>Pan, Yuanjiang</creator><creator>Ding, Chuanfan</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QF</scope><scope>7QO</scope><scope>7QP</scope><scope>7QQ</scope><scope>7QR</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7TA</scope><scope>7TB</scope><scope>7TK</scope><scope>7U5</scope><scope>7U7</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F1W</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>H97</scope><scope>JG9</scope><scope>JQ2</scope><scope>K9.</scope><scope>KR7</scope><scope>L.G</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>201607</creationdate><title>Ortho-hydroxyl effect and proton transfer via ion-neutral complex: the fragmentation study of protonated imine resveratrol analogues in mass spectrometry</title><author>Yue, Lei ; Li, Jing ; Xie, Xiaodong ; Guo, Cheng ; Yin, Xinchi ; Yin, Qi ; Chen, Yinjuan ; Pan, Yuanjiang ; Ding, Chuanfan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4908-a99f7dbcbb58442b11732e3ffa92aba5967893b324cb834f3afc5bdf09682c833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>benzyl cation</topic><topic>Cations</topic><topic>Chlorination</topic><topic>Congeners</topic><topic>Fragmentation</topic><topic>imine resveratrol analogue</topic><topic>Imines</topic><topic>ion-neutral complex</topic><topic>Mass spectrometry</topic><topic>ortho-hydroxyl effect</topic><topic>Pathways</topic><topic>proton transfer</topic><topic>Rings (mathematics)</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yue, Lei</creatorcontrib><creatorcontrib>Li, Jing</creatorcontrib><creatorcontrib>Xie, Xiaodong</creatorcontrib><creatorcontrib>Guo, Cheng</creatorcontrib><creatorcontrib>Yin, Xinchi</creatorcontrib><creatorcontrib>Yin, Qi</creatorcontrib><creatorcontrib>Chen, Yinjuan</creatorcontrib><creatorcontrib>Pan, Yuanjiang</creatorcontrib><creatorcontrib>Ding, Chuanfan</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Toxicology Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Civil Engineering Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of mass spectrometry.</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yue, Lei</au><au>Li, Jing</au><au>Xie, Xiaodong</au><au>Guo, Cheng</au><au>Yin, Xinchi</au><au>Yin, Qi</au><au>Chen, Yinjuan</au><au>Pan, Yuanjiang</au><au>Ding, Chuanfan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ortho-hydroxyl effect and proton transfer via ion-neutral complex: the fragmentation study of protonated imine resveratrol analogues in mass spectrometry</atitle><jtitle>Journal of mass spectrometry.</jtitle><addtitle>J. Mass Spectrom</addtitle><date>2016-07</date><risdate>2016</risdate><volume>51</volume><issue>7</issue><spage>518</spage><epage>523</epage><pages>518-523</pages><issn>1076-5174</issn><eissn>1096-9888</eissn><abstract>The fragmentation pathways of protonated imine resveratrol analogues in the gas‐phase were investigated by electrospray ionization–tandem mass spectrometry. Benzyl cations were formed in the imine resveratrol analogues that had an ortho‐hydroxyl group on the benzene ring A. The specific elimination of the quinomethane neutral, CH2 = C6H4 = O, from the two isomeric ions [M1 + H]+ and [M3 + H]+ via the corresponding ion–neutral complexes was observed. The fragmentation pathway for the related meta‐isomer, ion [M2 + H]+ and the other congeners was not observed. Accurate mass measurements and additional experiments carried out with a chlorinated analogue and the trideuterated isotopolog of M1 supported the overall interpretation of the fragmentation phenomena observed. It is very helpful for understanding the intriguing roles of ortho‐hydroxyl effect and ion–neutral complexes in fragmentation reactions and enriching the knowledge of the gas‐phase chemistry of the benzyl cation. Copyright © 2016 John Wiley & Sons, Ltd.</abstract><cop>England</cop><pub>Blackwell Publishing Ltd</pub><pmid>27434810</pmid><doi>10.1002/jms.3778</doi><tpages>6</tpages></addata></record> |
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| subjects | benzyl cation Cations Chlorination Congeners Fragmentation imine resveratrol analogue Imines ion-neutral complex Mass spectrometry ortho-hydroxyl effect Pathways proton transfer Rings (mathematics) |
| title | Ortho-hydroxyl effect and proton transfer via ion-neutral complex: the fragmentation study of protonated imine resveratrol analogues in mass spectrometry |
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