Fluorous Effects in Amide-Based Receptors for Anions
Hybrid receptors designed to recognize both the sulfonate headgroup and the fluorous tail of perfluorooctanesulfonate (CF3(CF2)7SO3 −, “PFOS”) were prepared by coupling fluorinated carboxylic acids onto poly(aminomethyl)benzene scaffolds. Binding to PFOS, CF3SO3 −, p-TsO−, and Cl− was monitored by 1...
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| Veröffentlicht in: | Journal of organic chemistry 2009-05, Vol.74 (10), p.3706-3710 |
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| container_title | Journal of organic chemistry |
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| creator | Gavette, Jesse V McGrath, Jacqueline M Spuches, Anne M Sargent, Andrew L Allen, William E |
| description | Hybrid receptors designed to recognize both the sulfonate headgroup and the fluorous tail of perfluorooctanesulfonate (CF3(CF2)7SO3 −, “PFOS”) were prepared by coupling fluorinated carboxylic acids onto poly(aminomethyl)benzene scaffolds. Binding to PFOS, CF3SO3 −, p-TsO−, and Cl− was monitored by 1H NMR and isothermal titration calorimetry (ITC). In chloroform solvent, hydrogen-bonding to anions is accompanied by downfield shifts in the amide NH protons of the fluorinated receptors and by evolution of heat. Association constants for 1:1 complexation (K assoc) are >1000 M−1. An analogous hydrocarbon receptor binds weakly to anionic guests (K assoc < 50 M−1). Ab initio calculations indicate that the differences in 1:1 binding strengths between fluorous and nonfluorous hosts cannot be ascribed to differences in NH donor acidities. |
| doi_str_mv | 10.1021/jo9000788 |
| format | Article |
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Org. Chem</addtitle><description>Hybrid receptors designed to recognize both the sulfonate headgroup and the fluorous tail of perfluorooctanesulfonate (CF3(CF2)7SO3 −, “PFOS”) were prepared by coupling fluorinated carboxylic acids onto poly(aminomethyl)benzene scaffolds. Binding to PFOS, CF3SO3 −, p-TsO−, and Cl− was monitored by 1H NMR and isothermal titration calorimetry (ITC). In chloroform solvent, hydrogen-bonding to anions is accompanied by downfield shifts in the amide NH protons of the fluorinated receptors and by evolution of heat. Association constants for 1:1 complexation (K assoc) are >1000 M−1. An analogous hydrocarbon receptor binds weakly to anionic guests (K assoc < 50 M−1). Ab initio calculations indicate that the differences in 1:1 binding strengths between fluorous and nonfluorous hosts cannot be ascribed to differences in NH donor acidities.</description><subject>Alkanesulfonic Acids - chemistry</subject><subject>Amides - chemistry</subject><subject>Chemistry</subject><subject>Coordination compounds</subject><subject>Exact sciences and technology</subject><subject>Fluorocarbons - chemistry</subject><subject>Inorganic chemistry and origins of life</subject><subject>Isoelectric Focusing</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Substrate Specificity</subject><subject>Thermodynamics</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M1Kw0AUBeBBFFurC19AslFwEZ2fTCazbEurQkEQXYfp5A6kJJk6N1n49o40tBtXd_Nx7uEQcsvoE6OcPe-8ppSqojgjUyY5TXNNs3MypZTzVPBcTMgV4i4aKqW8JBOmhSxkwaYkWzeDD37AZOUc2B6TukvmbV1BujAIVfIBFva9D5g4H5J5V_sOr8mFMw3CzXhn5Gu9-ly-ppv3l7flfJMakYk-BWGMLjSXXGZUMgXOuQpMzkSlmK6osKKIRSFjgmurjM6M5q6SLN8KLiKbkYdD7j747wGwL9saLTSN6SBWLnPFOVdKRfh4gDZ4xACu3Ie6NeGnZLT8m6g8ThTt3Rg6bFuoTnLcJIL7ERi0pnHBdLbGo-Ms01Tl8uSMxZg_hC5u8c_DX10Mdu4</recordid><startdate>20090515</startdate><enddate>20090515</enddate><creator>Gavette, Jesse V</creator><creator>McGrath, Jacqueline M</creator><creator>Spuches, Anne M</creator><creator>Sargent, Andrew L</creator><creator>Allen, William E</creator><general>American Chemical Society</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>7X8</scope></search><sort><creationdate>20090515</creationdate><title>Fluorous Effects in Amide-Based Receptors for Anions</title><author>Gavette, Jesse V ; McGrath, Jacqueline M ; Spuches, Anne M ; Sargent, Andrew L ; Allen, William E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a343t-e3aa989252540517efffdea613d719d03c38904e41329c7a94a92fd516b323613</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alkanesulfonic Acids - chemistry</topic><topic>Amides - chemistry</topic><topic>Chemistry</topic><topic>Coordination compounds</topic><topic>Exact sciences and technology</topic><topic>Fluorocarbons - chemistry</topic><topic>Inorganic chemistry and origins of life</topic><topic>Isoelectric Focusing</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Substrate Specificity</topic><topic>Thermodynamics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gavette, Jesse V</creatorcontrib><creatorcontrib>McGrath, Jacqueline M</creatorcontrib><creatorcontrib>Spuches, Anne M</creatorcontrib><creatorcontrib>Sargent, Andrew L</creatorcontrib><creatorcontrib>Allen, William E</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>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gavette, Jesse V</au><au>McGrath, Jacqueline M</au><au>Spuches, Anne M</au><au>Sargent, Andrew L</au><au>Allen, William E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Fluorous Effects in Amide-Based Receptors for Anions</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2009-05-15</date><risdate>2009</risdate><volume>74</volume><issue>10</issue><spage>3706</spage><epage>3710</epage><pages>3706-3710</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Hybrid receptors designed to recognize both the sulfonate headgroup and the fluorous tail of perfluorooctanesulfonate (CF3(CF2)7SO3 −, “PFOS”) were prepared by coupling fluorinated carboxylic acids onto poly(aminomethyl)benzene scaffolds. Binding to PFOS, CF3SO3 −, p-TsO−, and Cl− was monitored by 1H NMR and isothermal titration calorimetry (ITC). In chloroform solvent, hydrogen-bonding to anions is accompanied by downfield shifts in the amide NH protons of the fluorinated receptors and by evolution of heat. Association constants for 1:1 complexation (K assoc) are >1000 M−1. An analogous hydrocarbon receptor binds weakly to anionic guests (K assoc < 50 M−1). 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| subjects | Alkanesulfonic Acids - chemistry Amides - chemistry Chemistry Coordination compounds Exact sciences and technology Fluorocarbons - chemistry Inorganic chemistry and origins of life Isoelectric Focusing Noncondensed benzenic compounds Organic chemistry Preparations and properties Substrate Specificity Thermodynamics |
| title | Fluorous Effects in Amide-Based Receptors for Anions |
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