Structural Characterization of Methylenedianiline Regioisomers by Ion Mobility-Mass Spectrometry, Tandem Mass Spectrometry, and Computational Strategies. 2. Electrospray Spectra of 3‑Ring and 4‑Ring Isomers
Building on results from our previous study of 2-ring methylenedianiline (MDA), a combined mass spectrometry approach utilizing ion mobility-mass spectrometry (IM-MS) and tandem mass spectrometry (MS/MS) coupled with computational methods enables the structural characterization of purified 3-ring an...
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| Veröffentlicht in: | Analytical chemistry (Washington) 2015-06, Vol.87 (12), p.6288-6296 |
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| creator | Stow, Sarah M Onifer, Tiffany M Forsythe, Jay G Nefzger, Hartmut Kwiecien, Nicholas W May, Jody C McLean, John A Hercules, David M |
| description | Building on results from our previous study of 2-ring methylenedianiline (MDA), a combined mass spectrometry approach utilizing ion mobility-mass spectrometry (IM-MS) and tandem mass spectrometry (MS/MS) coupled with computational methods enables the structural characterization of purified 3-ring and 4-ring MDA regioisomers in this current study. The preferred site of protonation for the 3-ring and 4-ring MDA was determined to be on the amino groups. Additionally, the location of the protonated amine along the MDA multimer was found to influence the gas phase stability of these molecules. Fragmentation mechanisms similar to the 2-ring MDA species were observed for both the 3-ring and 4-ring MDA. The structural characterization of 3-ring and 4-ring MDA isomers using modern MS techniques may aid polyurethane synthesis by the characterization of industrial grade MDA, multimeric MDA species, and methylene diphenyl diisocyanate (MDI) mixtures. |
| doi_str_mv | 10.1021/acs.analchem.5b01084 |
| format | Article |
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Electrospray Spectra of 3‑Ring and 4‑Ring Isomers</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Stow, Sarah M ; Onifer, Tiffany M ; Forsythe, Jay G ; Nefzger, Hartmut ; Kwiecien, Nicholas W ; May, Jody C ; McLean, John A ; Hercules, David M</creator><creatorcontrib>Stow, Sarah M ; Onifer, Tiffany M ; Forsythe, Jay G ; Nefzger, Hartmut ; Kwiecien, Nicholas W ; May, Jody C ; McLean, John A ; Hercules, David M</creatorcontrib><description>Building on results from our previous study of 2-ring methylenedianiline (MDA), a combined mass spectrometry approach utilizing ion mobility-mass spectrometry (IM-MS) and tandem mass spectrometry (MS/MS) coupled with computational methods enables the structural characterization of purified 3-ring and 4-ring MDA regioisomers in this current study. The preferred site of protonation for the 3-ring and 4-ring MDA was determined to be on the amino groups. Additionally, the location of the protonated amine along the MDA multimer was found to influence the gas phase stability of these molecules. Fragmentation mechanisms similar to the 2-ring MDA species were observed for both the 3-ring and 4-ring MDA. The structural characterization of 3-ring and 4-ring MDA isomers using modern MS techniques may aid polyurethane synthesis by the characterization of industrial grade MDA, multimeric MDA species, and methylene diphenyl diisocyanate (MDI) mixtures.</description><identifier>ISSN: 0003-2700</identifier><identifier>EISSN: 1520-6882</identifier><identifier>DOI: 10.1021/acs.analchem.5b01084</identifier><identifier>PMID: 25971782</identifier><identifier>CODEN: ANCHAM</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Analytical chemistry ; Aniline Compounds - chemistry ; Computation ; Computer Simulation ; Construction ; Isomers ; Mass spectrometry ; Methylene ; Molecular Structure ; Molecules ; Polyurethane ; Spectrometry ; Spectrometry, Mass, Electrospray Ionization ; Spectroscopy ; Stereoisomerism ; Structural analysis ; Tandem Mass Spectrometry</subject><ispartof>Analytical chemistry (Washington), 2015-06, Vol.87 (12), p.6288-6296</ispartof><rights>Copyright © American Chemical Society</rights><rights>Copyright American Chemical Society Jun 16, 2015</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a510t-fbb1bd08a778cef01059813791224df4a67f557f2bf7e4a65668b7c81bb0e8da3</citedby><cites>FETCH-LOGICAL-a510t-fbb1bd08a778cef01059813791224df4a67f557f2bf7e4a65668b7c81bb0e8da3</cites></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.analchem.5b01084$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.analchem.5b01084$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25971782$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Stow, Sarah M</creatorcontrib><creatorcontrib>Onifer, Tiffany M</creatorcontrib><creatorcontrib>Forsythe, Jay G</creatorcontrib><creatorcontrib>Nefzger, Hartmut</creatorcontrib><creatorcontrib>Kwiecien, Nicholas W</creatorcontrib><creatorcontrib>May, Jody C</creatorcontrib><creatorcontrib>McLean, John A</creatorcontrib><creatorcontrib>Hercules, David M</creatorcontrib><title>Structural Characterization of Methylenedianiline Regioisomers by Ion Mobility-Mass Spectrometry, Tandem Mass Spectrometry, and Computational Strategies. 2. Electrospray Spectra of 3‑Ring and 4‑Ring Isomers</title><title>Analytical chemistry (Washington)</title><addtitle>Anal. Chem</addtitle><description>Building on results from our previous study of 2-ring methylenedianiline (MDA), a combined mass spectrometry approach utilizing ion mobility-mass spectrometry (IM-MS) and tandem mass spectrometry (MS/MS) coupled with computational methods enables the structural characterization of purified 3-ring and 4-ring MDA regioisomers in this current study. The preferred site of protonation for the 3-ring and 4-ring MDA was determined to be on the amino groups. Additionally, the location of the protonated amine along the MDA multimer was found to influence the gas phase stability of these molecules. Fragmentation mechanisms similar to the 2-ring MDA species were observed for both the 3-ring and 4-ring MDA. The structural characterization of 3-ring and 4-ring MDA isomers using modern MS techniques may aid polyurethane synthesis by the characterization of industrial grade MDA, multimeric MDA species, and methylene diphenyl diisocyanate (MDI) mixtures.</description><subject>Analytical chemistry</subject><subject>Aniline Compounds - chemistry</subject><subject>Computation</subject><subject>Computer Simulation</subject><subject>Construction</subject><subject>Isomers</subject><subject>Mass spectrometry</subject><subject>Methylene</subject><subject>Molecular Structure</subject><subject>Molecules</subject><subject>Polyurethane</subject><subject>Spectrometry</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Spectroscopy</subject><subject>Stereoisomerism</subject><subject>Structural analysis</subject><subject>Tandem Mass Spectrometry</subject><issn>0003-2700</issn><issn>1520-6882</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kt-K1DAUxoso7rj6BiIBb7yw9STTNpkbQYZVB3YQdtfrcNKmM1napiapUK98BV_NR_BJzPxb_yBehcP5ne98OXxJ8pRCRoHRV1j5DHtsq63uskIBBZHfS2a0YJCWQrD7yQwA5injAGfJI-9vASgFWj5Mzlix4JQLNku-Xwc3VmF02JLlFh1WQTvzBYOxPbENWeuwnVrd69pgb1rTa3KlN8YabzvtPFETWUVybVVshildo_fketBVcBEIbnpJbrCvdUf-0YkNsrTdMIb9vmghusEQ9bXPCMvIRbvH_eBwOs7iztX8x9dvV6bf7BXyU7E6eHqcPGiw9frJ8T1PPr69uFm-Ty8_vFst31ymWFAIaaMUVTUI5FxUuon3KxaCzvmCMpbXTY4lb4qCN0w1XMeqKEuheCWoUqBFjfPz5PVBdxhVp-tK99FdKwdnOnSTtGjkn53ebOXGfpZFmbO4LQq8OAo4-2nUPsjO-Eq3Lfbajl5SDgteFizPI_r8L_TWji5eLFLlggIXOdBI5QeqijfzTjd3ZijIXWhkDI08hUYeQxPHnv3-kbuhU0oiAAdgN_5r8f80fwKvUNi9</recordid><startdate>20150616</startdate><enddate>20150616</enddate><creator>Stow, Sarah M</creator><creator>Onifer, Tiffany M</creator><creator>Forsythe, Jay G</creator><creator>Nefzger, Hartmut</creator><creator>Kwiecien, Nicholas W</creator><creator>May, Jody C</creator><creator>McLean, John A</creator><creator>Hercules, David M</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QF</scope><scope>7QO</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7TA</scope><scope>7TB</scope><scope>7TM</scope><scope>7U5</scope><scope>7U7</scope><scope>7U9</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>H94</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope><scope>5PM</scope></search><sort><creationdate>20150616</creationdate><title>Structural Characterization of Methylenedianiline Regioisomers by Ion Mobility-Mass Spectrometry, Tandem Mass Spectrometry, and Computational Strategies. 2. Electrospray Spectra of 3‑Ring and 4‑Ring Isomers</title><author>Stow, Sarah M ; Onifer, Tiffany M ; Forsythe, Jay G ; Nefzger, Hartmut ; Kwiecien, Nicholas W ; May, Jody C ; McLean, John A ; Hercules, David M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a510t-fbb1bd08a778cef01059813791224df4a67f557f2bf7e4a65668b7c81bb0e8da3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Analytical chemistry</topic><topic>Aniline Compounds - chemistry</topic><topic>Computation</topic><topic>Computer Simulation</topic><topic>Construction</topic><topic>Isomers</topic><topic>Mass spectrometry</topic><topic>Methylene</topic><topic>Molecular Structure</topic><topic>Molecules</topic><topic>Polyurethane</topic><topic>Spectrometry</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Spectroscopy</topic><topic>Stereoisomerism</topic><topic>Structural analysis</topic><topic>Tandem Mass Spectrometry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Stow, Sarah M</creatorcontrib><creatorcontrib>Onifer, Tiffany M</creatorcontrib><creatorcontrib>Forsythe, Jay G</creatorcontrib><creatorcontrib>Nefzger, Hartmut</creatorcontrib><creatorcontrib>Kwiecien, Nicholas W</creatorcontrib><creatorcontrib>May, Jody C</creatorcontrib><creatorcontrib>McLean, John A</creatorcontrib><creatorcontrib>Hercules, David M</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Ceramic 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>Nucleic Acids Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</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>AIDS and Cancer Research Abstracts</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Civil Engineering Abstracts</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>PubMed Central (Full Participant titles)</collection><jtitle>Analytical chemistry (Washington)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Stow, Sarah M</au><au>Onifer, Tiffany M</au><au>Forsythe, Jay G</au><au>Nefzger, Hartmut</au><au>Kwiecien, Nicholas W</au><au>May, Jody C</au><au>McLean, John A</au><au>Hercules, David M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structural Characterization of Methylenedianiline Regioisomers by Ion Mobility-Mass Spectrometry, Tandem Mass Spectrometry, and Computational Strategies. 2. Electrospray Spectra of 3‑Ring and 4‑Ring Isomers</atitle><jtitle>Analytical chemistry (Washington)</jtitle><addtitle>Anal. Chem</addtitle><date>2015-06-16</date><risdate>2015</risdate><volume>87</volume><issue>12</issue><spage>6288</spage><epage>6296</epage><pages>6288-6296</pages><issn>0003-2700</issn><eissn>1520-6882</eissn><coden>ANCHAM</coden><abstract>Building on results from our previous study of 2-ring methylenedianiline (MDA), a combined mass spectrometry approach utilizing ion mobility-mass spectrometry (IM-MS) and tandem mass spectrometry (MS/MS) coupled with computational methods enables the structural characterization of purified 3-ring and 4-ring MDA regioisomers in this current study. The preferred site of protonation for the 3-ring and 4-ring MDA was determined to be on the amino groups. Additionally, the location of the protonated amine along the MDA multimer was found to influence the gas phase stability of these molecules. Fragmentation mechanisms similar to the 2-ring MDA species were observed for both the 3-ring and 4-ring MDA. The structural characterization of 3-ring and 4-ring MDA isomers using modern MS techniques may aid polyurethane synthesis by the characterization of industrial grade MDA, multimeric MDA species, and methylene diphenyl diisocyanate (MDI) mixtures.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25971782</pmid><doi>10.1021/acs.analchem.5b01084</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Analytical chemistry Aniline Compounds - chemistry Computation Computer Simulation Construction Isomers Mass spectrometry Methylene Molecular Structure Molecules Polyurethane Spectrometry Spectrometry, Mass, Electrospray Ionization Spectroscopy Stereoisomerism Structural analysis Tandem Mass Spectrometry |
| title | Structural Characterization of Methylenedianiline Regioisomers by Ion Mobility-Mass Spectrometry, Tandem Mass Spectrometry, and Computational Strategies. 2. Electrospray Spectra of 3‑Ring and 4‑Ring Isomers |
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