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Unusual Complex Formation and Chemical Reaction of Haloacetate Anion on the Exterior Surface of Cucurbit[6]uril in the Gas Phase
Noncovalent interactions of cucurbit[6]uril (CB[6]) with haloacetate and halide anions are investigated in the gas phase using electrospray ionization ion mobility mass spectrometry. Strong noncovalent interactions of monoiodoacetate, monobromoacetate, monochloroacetate, dichloroacetate, and trichlo...
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| Published in: | Journal of the American Society for Mass Spectrometry 2012-10, Vol.23 (10), p.1786-1793 |
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| Main Authors: | , , , , , |
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| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c445t-67284512e5b6344cd15a0763f0ec96cb485483389c8fc5b805d929280092deb3 |
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| cites | cdi_FETCH-LOGICAL-c445t-67284512e5b6344cd15a0763f0ec96cb485483389c8fc5b805d929280092deb3 |
| container_end_page | 1793 |
| container_issue | 10 |
| container_start_page | 1786 |
| container_title | Journal of the American Society for Mass Spectrometry |
| container_volume | 23 |
| creator | Choi, Tae Su Ko, Jae Yoon Heo, Sung Woo Ko, Young Ho Kim, Kimoon Kim, Hugh I. |
| description | Noncovalent interactions of cucurbit[6]uril (CB[6]) with haloacetate and halide anions are investigated in the gas phase using electrospray ionization ion mobility mass spectrometry. Strong noncovalent interactions of monoiodoacetate, monobromoacetate, monochloroacetate, dichloroacetate, and trichloroacetate on the exterior surface of CB[6] are observed in the negative mode electrospray ionization mass spectra. The strong binding energy of the complex allows intramolecular S
N
2 reaction of haloacetate, which yields externally bound CB[6]-halide complex, by collisional activation. Utilizing ion mobility technique, structures of exteriorly bound CB[6] complexes of haloacetate and halide anions are confirmed. Theoretically determined low energy structures using density functional theory (DFT) further support results from ion mobility studies. The DFT calculation reveals that the binding energy and conformation of haloacetate on the CB[6] surface affect the efficiency of the intramolecular S
N
2 reaction of haloacetate, which correlate well with the experimental observation. |
| doi_str_mv | 10.1007/s13361-012-0443-6 |
| format | article |
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N
2 reaction of haloacetate, which yields externally bound CB[6]-halide complex, by collisional activation. Utilizing ion mobility technique, structures of exteriorly bound CB[6] complexes of haloacetate and halide anions are confirmed. Theoretically determined low energy structures using density functional theory (DFT) further support results from ion mobility studies. The DFT calculation reveals that the binding energy and conformation of haloacetate on the CB[6] surface affect the efficiency of the intramolecular S
N
2 reaction of haloacetate, which correlate well with the experimental observation.</description><identifier>ISSN: 1044-0305</identifier><identifier>EISSN: 1879-1123</identifier><identifier>DOI: 10.1007/s13361-012-0443-6</identifier><identifier>PMID: 22864828</identifier><language>eng</language><publisher>New York: Springer-Verlag</publisher><subject>Analytical Chemistry ; Anions ; Binding energy ; Bioinformatics ; Biotechnology ; Bridged-Ring Compounds - chemistry ; Chemical bonds ; Chemistry ; Chemistry and Materials Science ; Chloroacetates - chemistry ; Complex formation ; Computer Simulation ; Density functional theory ; Electrospraying ; Energy consumption ; Exact sciences and technology ; Gases - chemistry ; Imidazoles - chemistry ; Ionic mobility ; Ionization ; Ions ; Mass spectra ; Mass spectrometry ; Models, Molecular ; Organic Chemistry ; Proteomics ; Reactivity and mechanisms ; Research Article ; Spectrometry, Mass, Electrospray Ionization ; Thermodynamics</subject><ispartof>Journal of the American Society for Mass Spectrometry, 2012-10, Vol.23 (10), p.1786-1793</ispartof><rights>American Society for Mass Spectrometry 2012</rights><rights>2014 INIST-CNRS</rights><rights>Journal of The American Society for Mass Spectrometry is a copyright of Springer, 2012.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c445t-67284512e5b6344cd15a0763f0ec96cb485483389c8fc5b805d929280092deb3</citedby><cites>FETCH-LOGICAL-c445t-67284512e5b6344cd15a0763f0ec96cb485483389c8fc5b805d929280092deb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26507168$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22864828$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Choi, Tae Su</creatorcontrib><creatorcontrib>Ko, Jae Yoon</creatorcontrib><creatorcontrib>Heo, Sung Woo</creatorcontrib><creatorcontrib>Ko, Young Ho</creatorcontrib><creatorcontrib>Kim, Kimoon</creatorcontrib><creatorcontrib>Kim, Hugh I.</creatorcontrib><title>Unusual Complex Formation and Chemical Reaction of Haloacetate Anion on the Exterior Surface of Cucurbit[6]uril in the Gas Phase</title><title>Journal of the American Society for Mass Spectrometry</title><addtitle>J. Am. Soc. Mass Spectrom</addtitle><addtitle>J Am Soc Mass Spectrom</addtitle><description>Noncovalent interactions of cucurbit[6]uril (CB[6]) with haloacetate and halide anions are investigated in the gas phase using electrospray ionization ion mobility mass spectrometry. Strong noncovalent interactions of monoiodoacetate, monobromoacetate, monochloroacetate, dichloroacetate, and trichloroacetate on the exterior surface of CB[6] are observed in the negative mode electrospray ionization mass spectra. The strong binding energy of the complex allows intramolecular S
N
2 reaction of haloacetate, which yields externally bound CB[6]-halide complex, by collisional activation. Utilizing ion mobility technique, structures of exteriorly bound CB[6] complexes of haloacetate and halide anions are confirmed. Theoretically determined low energy structures using density functional theory (DFT) further support results from ion mobility studies. The DFT calculation reveals that the binding energy and conformation of haloacetate on the CB[6] surface affect the efficiency of the intramolecular S
N
2 reaction of haloacetate, which correlate well with the experimental observation.</description><subject>Analytical Chemistry</subject><subject>Anions</subject><subject>Binding energy</subject><subject>Bioinformatics</subject><subject>Biotechnology</subject><subject>Bridged-Ring Compounds - chemistry</subject><subject>Chemical bonds</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chloroacetates - chemistry</subject><subject>Complex formation</subject><subject>Computer Simulation</subject><subject>Density functional theory</subject><subject>Electrospraying</subject><subject>Energy consumption</subject><subject>Exact sciences and technology</subject><subject>Gases - chemistry</subject><subject>Imidazoles - chemistry</subject><subject>Ionic mobility</subject><subject>Ionization</subject><subject>Ions</subject><subject>Mass spectra</subject><subject>Mass spectrometry</subject><subject>Models, Molecular</subject><subject>Organic Chemistry</subject><subject>Proteomics</subject><subject>Reactivity and mechanisms</subject><subject>Research Article</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Thermodynamics</subject><issn>1044-0305</issn><issn>1879-1123</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp1kVtrFTEUhYNYbK3-AF8kIAVfxu5cJ_NYhl6EgqXWJ5GQyWQ8KTOTYzKB-uZPN6dzvCD4tDdrf3tlk4XQKwLvCEB9mghjklRAaAWcs0o-QUdE1U1FCGVPS1_UChiIQ_Q8pXsAUkNTP0OHlCrJFVVH6MenOadsRtyGaTu6B3wR4mQWH2Zs5h63Gzd5W8a3zthHNQz4yozBWLeYxeGz-VGc8bJx-PxhcdGHiD_mOBRiB7fZ5tj55bP8kqMfsV_RS5PwzcYk9wIdDGZM7uW-HqO7i_O79qq6_nD5vj27riznYqlkTRUXhDrRSca57YkwUEs2gLONtB1XgivGVGPVYEWnQPQNbagCaGjvOnaM3q622xi-ZZcWPflk3Tia2YWcNAEFknDW0IK--Qe9DznO5ThNGkFAKMJFochK2RhSim7Q2-gnE78XK71LR6_p6JKO3qWjZdl5vXfO3eT63xu_4ijAyR4wqfz6EM1sffrDSQE1kTuOrlwqo_mri3-d-N_XfwK6TaWP</recordid><startdate>20121001</startdate><enddate>20121001</enddate><creator>Choi, Tae Su</creator><creator>Ko, Jae Yoon</creator><creator>Heo, Sung Woo</creator><creator>Ko, Young Ho</creator><creator>Kim, Kimoon</creator><creator>Kim, Hugh I.</creator><general>Springer-Verlag</general><general>Elsevier</general><general>Springer Nature B.V</general><scope>IQODW</scope><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>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FE</scope><scope>8FG</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>ARAPS</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>M2O</scope><scope>MBDVC</scope><scope>P5Z</scope><scope>P62</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope></search><sort><creationdate>20121001</creationdate><title>Unusual Complex Formation and Chemical Reaction of Haloacetate Anion on the Exterior Surface of Cucurbit[6]uril in the Gas Phase</title><author>Choi, Tae Su ; Ko, Jae Yoon ; Heo, Sung Woo ; Ko, Young Ho ; Kim, Kimoon ; Kim, Hugh I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c445t-67284512e5b6344cd15a0763f0ec96cb485483389c8fc5b805d929280092deb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Analytical Chemistry</topic><topic>Anions</topic><topic>Binding energy</topic><topic>Bioinformatics</topic><topic>Biotechnology</topic><topic>Bridged-Ring Compounds - chemistry</topic><topic>Chemical bonds</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chloroacetates - chemistry</topic><topic>Complex formation</topic><topic>Computer Simulation</topic><topic>Density functional theory</topic><topic>Electrospraying</topic><topic>Energy consumption</topic><topic>Exact sciences and technology</topic><topic>Gases - chemistry</topic><topic>Imidazoles - chemistry</topic><topic>Ionic mobility</topic><topic>Ionization</topic><topic>Ions</topic><topic>Mass spectra</topic><topic>Mass spectrometry</topic><topic>Models, Molecular</topic><topic>Organic Chemistry</topic><topic>Proteomics</topic><topic>Reactivity and mechanisms</topic><topic>Research Article</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Thermodynamics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Choi, Tae Su</creatorcontrib><creatorcontrib>Ko, Jae Yoon</creatorcontrib><creatorcontrib>Heo, Sung Woo</creatorcontrib><creatorcontrib>Ko, Young Ho</creatorcontrib><creatorcontrib>Kim, Kimoon</creatorcontrib><creatorcontrib>Kim, Hugh I.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>Advanced Technologies & Aerospace Collection</collection><collection>ProQuest Central Essentials</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>ProQuest research library</collection><collection>Research Library (Corporate)</collection><collection>ProQuest advanced technologies & aerospace journals</collection><collection>ProQuest Advanced Technologies & Aerospace Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Society for Mass Spectrometry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Choi, Tae Su</au><au>Ko, Jae Yoon</au><au>Heo, Sung Woo</au><au>Ko, Young Ho</au><au>Kim, Kimoon</au><au>Kim, Hugh I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Unusual Complex Formation and Chemical Reaction of Haloacetate Anion on the Exterior Surface of Cucurbit[6]uril in the Gas Phase</atitle><jtitle>Journal of the American Society for Mass Spectrometry</jtitle><stitle>J. Am. Soc. Mass Spectrom</stitle><addtitle>J Am Soc Mass Spectrom</addtitle><date>2012-10-01</date><risdate>2012</risdate><volume>23</volume><issue>10</issue><spage>1786</spage><epage>1793</epage><pages>1786-1793</pages><issn>1044-0305</issn><eissn>1879-1123</eissn><abstract>Noncovalent interactions of cucurbit[6]uril (CB[6]) with haloacetate and halide anions are investigated in the gas phase using electrospray ionization ion mobility mass spectrometry. Strong noncovalent interactions of monoiodoacetate, monobromoacetate, monochloroacetate, dichloroacetate, and trichloroacetate on the exterior surface of CB[6] are observed in the negative mode electrospray ionization mass spectra. The strong binding energy of the complex allows intramolecular S
N
2 reaction of haloacetate, which yields externally bound CB[6]-halide complex, by collisional activation. Utilizing ion mobility technique, structures of exteriorly bound CB[6] complexes of haloacetate and halide anions are confirmed. Theoretically determined low energy structures using density functional theory (DFT) further support results from ion mobility studies. The DFT calculation reveals that the binding energy and conformation of haloacetate on the CB[6] surface affect the efficiency of the intramolecular S
N
2 reaction of haloacetate, which correlate well with the experimental observation.</abstract><cop>New York</cop><pub>Springer-Verlag</pub><pmid>22864828</pmid><doi>10.1007/s13361-012-0443-6</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Analytical Chemistry Anions Binding energy Bioinformatics Biotechnology Bridged-Ring Compounds - chemistry Chemical bonds Chemistry Chemistry and Materials Science Chloroacetates - chemistry Complex formation Computer Simulation Density functional theory Electrospraying Energy consumption Exact sciences and technology Gases - chemistry Imidazoles - chemistry Ionic mobility Ionization Ions Mass spectra Mass spectrometry Models, Molecular Organic Chemistry Proteomics Reactivity and mechanisms Research Article Spectrometry, Mass, Electrospray Ionization Thermodynamics |
| title | Unusual Complex Formation and Chemical Reaction of Haloacetate Anion on the Exterior Surface of Cucurbit[6]uril in the Gas Phase |
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