Calix[4]pyrrole as a Chloride Anion Receptor: Solvent and Countercation Effects
The interaction of calixpyrrole with several chloride salts has been studied in the solid state by X-ray crystallography as well as in solution by isothermal titration calorimetry (ITC) and 1H NMR spectroscopic titrations. The titration results in dimethylsulfoxide, acetonitrile, nitromethane, 1,2-d...
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| Veröffentlicht in: | Journal of the American Chemical Society 2006-09, Vol.128 (37), p.12281-12288 |
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| container_title | Journal of the American Chemical Society |
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| creator | Sessler, Jonathan L Gross, Dustin E Cho, Won-Seob Lynch, Vincent M Schmidtchen, Franz P Bates, Gareth W Light, Mark E Gale, Philip A |
| description | The interaction of calixpyrrole with several chloride salts has been studied in the solid state by X-ray crystallography as well as in solution by isothermal titration calorimetry (ITC) and 1H NMR spectroscopic titrations. The titration results in dimethylsulfoxide, acetonitrile, nitromethane, 1,2-dichloroethane, and dichloromethane, carried out using various chloride salts, specifically tetraethylammonium (TEA), tetrapropylammonium (TPA), tetrabutylammonium (TBA), tetraethylphosphonium (TEP), tetrabutylphosphonium (TBP), and tetraphenylphosphonium (TPhP), showed no dependence on method of measurement. The resulting affinity constants (K a), on the other hand, were found to be highly dependent on the choice of solvent with K a's ranging from 102−105 M-1 being recorded in the test solvents used for this study. In dichloromethane, a strong dependence on the countercation was also seen, with the K a's for the interaction with chloride ranging from 102−104 M-1. In the case of TPA, TBA, and TBP, the ITC data could not be fit to a 1:1 binding profile. |
| doi_str_mv | 10.1021/ja064012h |
| format | Article |
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The titration results in dimethylsulfoxide, acetonitrile, nitromethane, 1,2-dichloroethane, and dichloromethane, carried out using various chloride salts, specifically tetraethylammonium (TEA), tetrapropylammonium (TPA), tetrabutylammonium (TBA), tetraethylphosphonium (TEP), tetrabutylphosphonium (TBP), and tetraphenylphosphonium (TPhP), showed no dependence on method of measurement. The resulting affinity constants (K a), on the other hand, were found to be highly dependent on the choice of solvent with K a's ranging from 102−105 M-1 being recorded in the test solvents used for this study. In dichloromethane, a strong dependence on the countercation was also seen, with the K a's for the interaction with chloride ranging from 102−104 M-1. In the case of TPA, TBA, and TBP, the ITC data could not be fit to a 1:1 binding profile.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja064012h</identifier><identifier>PMID: 16967979</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Anions ; Calixarenes - chemistry ; Calixarenes - metabolism ; Calorimetry ; Chemistry ; Chlorides - chemistry ; Chlorides - metabolism ; Crystallography, X-Ray ; Exact sciences and technology ; General and physical chemistry ; Heterocyclic compounds ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Kinetics ; Models, Molecular ; Molecular Structure ; Organic chemistry ; Porphyrins - chemistry ; Porphyrins - metabolism ; Preparations and properties ; Quaternary Ammonium Compounds - chemistry ; Quaternary Ammonium Compounds - metabolism ; Solutions ; Titrimetry</subject><ispartof>Journal of the American Chemical Society, 2006-09, Vol.128 (37), p.12281-12288</ispartof><rights>Copyright © 2006 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a385t-b4431e74fb0f5bf75e21b43c8b12ca2884d893b8d3734ea581dd29a98423f9743</citedby><cites>FETCH-LOGICAL-a385t-b4431e74fb0f5bf75e21b43c8b12ca2884d893b8d3734ea581dd29a98423f9743</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/ja064012h$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja064012h$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27059,27907,27908,56721,56771</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18118655$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16967979$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sessler, Jonathan L</creatorcontrib><creatorcontrib>Gross, Dustin E</creatorcontrib><creatorcontrib>Cho, Won-Seob</creatorcontrib><creatorcontrib>Lynch, Vincent M</creatorcontrib><creatorcontrib>Schmidtchen, Franz P</creatorcontrib><creatorcontrib>Bates, Gareth W</creatorcontrib><creatorcontrib>Light, Mark E</creatorcontrib><creatorcontrib>Gale, Philip A</creatorcontrib><title>Calix[4]pyrrole as a Chloride Anion Receptor: Solvent and Countercation Effects</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>The interaction of calixpyrrole with several chloride salts has been studied in the solid state by X-ray crystallography as well as in solution by isothermal titration calorimetry (ITC) and 1H NMR spectroscopic titrations. The titration results in dimethylsulfoxide, acetonitrile, nitromethane, 1,2-dichloroethane, and dichloromethane, carried out using various chloride salts, specifically tetraethylammonium (TEA), tetrapropylammonium (TPA), tetrabutylammonium (TBA), tetraethylphosphonium (TEP), tetrabutylphosphonium (TBP), and tetraphenylphosphonium (TPhP), showed no dependence on method of measurement. The resulting affinity constants (K a), on the other hand, were found to be highly dependent on the choice of solvent with K a's ranging from 102−105 M-1 being recorded in the test solvents used for this study. In dichloromethane, a strong dependence on the countercation was also seen, with the K a's for the interaction with chloride ranging from 102−104 M-1. In the case of TPA, TBA, and TBP, the ITC data could not be fit to a 1:1 binding profile.</description><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Anions</subject><subject>Calixarenes - chemistry</subject><subject>Calixarenes - metabolism</subject><subject>Calorimetry</subject><subject>Chemistry</subject><subject>Chlorides - chemistry</subject><subject>Chlorides - metabolism</subject><subject>Crystallography, X-Ray</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Kinetics</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Porphyrins - chemistry</subject><subject>Porphyrins - metabolism</subject><subject>Preparations and properties</subject><subject>Quaternary Ammonium Compounds - chemistry</subject><subject>Quaternary Ammonium Compounds - metabolism</subject><subject>Solutions</subject><subject>Titrimetry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MtKw0AUBuBBFK3VhS8g2bhwEZ1rZuJOQr1RUNq6EhlOJjOYGpMyk0q7c-tr-iRGWtqNq8PhfPwcfoROCL4gmJLLKeCEY0LfdlCPCIpjQWiyi3oYYxpLlbADdBjCtFs5VWQfHZAkTWQq0x4aZVCVixf-Olt631Q2ghBBlL1VjS8LG13XZVNHI2vsrG381c_XdzRuqk9btxHURZQ187q13kD7xwbOWdOGI7TnoAr2eD376PlmMMnu4uHj7X12PYyBKdHGOeeMWMldjp3InRSWkpwzo3JCDVCleKFSlquCScYtCEWKgqaQKk6ZSyVnfXS-yjW-CcFbp2e-_AC_1ATrv170ppfOnq7sbJ5_2GIr10V04GwNIBionIfalGHrFCEqEaJz8cqVobWLzR38u04kk0JPnsZaPamJnKgHPdzmggl62sx93VXyz4O_CZ6FoA</recordid><startdate>20060920</startdate><enddate>20060920</enddate><creator>Sessler, Jonathan L</creator><creator>Gross, Dustin E</creator><creator>Cho, Won-Seob</creator><creator>Lynch, Vincent M</creator><creator>Schmidtchen, Franz P</creator><creator>Bates, Gareth W</creator><creator>Light, Mark E</creator><creator>Gale, Philip A</creator><general>American Chemical Society</general><scope>BSCLL</scope><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></search><sort><creationdate>20060920</creationdate><title>Calix[4]pyrrole as a Chloride Anion Receptor: Solvent and Countercation Effects</title><author>Sessler, Jonathan L ; Gross, Dustin E ; Cho, Won-Seob ; Lynch, Vincent M ; Schmidtchen, Franz P ; Bates, Gareth W ; Light, Mark E ; Gale, Philip A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a385t-b4431e74fb0f5bf75e21b43c8b12ca2884d893b8d3734ea581dd29a98423f9743</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Anions</topic><topic>Calixarenes - chemistry</topic><topic>Calixarenes - metabolism</topic><topic>Calorimetry</topic><topic>Chemistry</topic><topic>Chlorides - chemistry</topic><topic>Chlorides - metabolism</topic><topic>Crystallography, X-Ray</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Kinetics</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Porphyrins - chemistry</topic><topic>Porphyrins - metabolism</topic><topic>Preparations and properties</topic><topic>Quaternary Ammonium Compounds - chemistry</topic><topic>Quaternary Ammonium Compounds - metabolism</topic><topic>Solutions</topic><topic>Titrimetry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sessler, Jonathan L</creatorcontrib><creatorcontrib>Gross, Dustin E</creatorcontrib><creatorcontrib>Cho, Won-Seob</creatorcontrib><creatorcontrib>Lynch, Vincent M</creatorcontrib><creatorcontrib>Schmidtchen, Franz P</creatorcontrib><creatorcontrib>Bates, Gareth W</creatorcontrib><creatorcontrib>Light, Mark E</creatorcontrib><creatorcontrib>Gale, Philip A</creatorcontrib><collection>Istex</collection><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><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sessler, Jonathan L</au><au>Gross, Dustin E</au><au>Cho, Won-Seob</au><au>Lynch, Vincent M</au><au>Schmidtchen, Franz P</au><au>Bates, Gareth W</au><au>Light, Mark E</au><au>Gale, Philip A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Calix[4]pyrrole as a Chloride Anion Receptor: Solvent and Countercation Effects</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2006-09-20</date><risdate>2006</risdate><volume>128</volume><issue>37</issue><spage>12281</spage><epage>12288</epage><pages>12281-12288</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>The interaction of calixpyrrole with several chloride salts has been studied in the solid state by X-ray crystallography as well as in solution by isothermal titration calorimetry (ITC) and 1H NMR spectroscopic titrations. The titration results in dimethylsulfoxide, acetonitrile, nitromethane, 1,2-dichloroethane, and dichloromethane, carried out using various chloride salts, specifically tetraethylammonium (TEA), tetrapropylammonium (TPA), tetrabutylammonium (TBA), tetraethylphosphonium (TEP), tetrabutylphosphonium (TBP), and tetraphenylphosphonium (TPhP), showed no dependence on method of measurement. The resulting affinity constants (K a), on the other hand, were found to be highly dependent on the choice of solvent with K a's ranging from 102−105 M-1 being recorded in the test solvents used for this study. In dichloromethane, a strong dependence on the countercation was also seen, with the K a's for the interaction with chloride ranging from 102−104 M-1. In the case of TPA, TBA, and TBP, the ITC data could not be fit to a 1:1 binding profile.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16967979</pmid><doi>10.1021/ja064012h</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Anions Calixarenes - chemistry Calixarenes - metabolism Calorimetry Chemistry Chlorides - chemistry Chlorides - metabolism Crystallography, X-Ray Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Kinetics Models, Molecular Molecular Structure Organic chemistry Porphyrins - chemistry Porphyrins - metabolism Preparations and properties Quaternary Ammonium Compounds - chemistry Quaternary Ammonium Compounds - metabolism Solutions Titrimetry |
| title | Calix[4]pyrrole as a Chloride Anion Receptor: Solvent and Countercation Effects |
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