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Anion and cation binding by a new indole/pyridine/amine-based ion-pair receptor
A new ion-pair receptor bis(3-bromoindol-2-ylmethyl)(2-pyridylmethyl)amine ( 1) was synthesized and studied for its anion and cation binding behavior using ESI-MS and 1H NMR spectroscopy. Among halides, 1 exhibits the strongest binding with Cl − to form a 1:1 adduct ( K a = 1042 ± 21 in CD 3CN). Amo...
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| Published in: | Tetrahedron letters 2010-12, Vol.51 (50), p.6516-6520 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c339t-2e0939a1b86191419a617cbba7bc11eb13fa34e3e96c36ae18d56df56fa640913 |
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| cites | cdi_FETCH-LOGICAL-c339t-2e0939a1b86191419a617cbba7bc11eb13fa34e3e96c36ae18d56df56fa640913 |
| container_end_page | 6520 |
| container_issue | 50 |
| container_start_page | 6516 |
| container_title | Tetrahedron letters |
| container_volume | 51 |
| creator | Skala, Kristin N. Perkins, Katelyn G. Ali, Amna Kutlik, Robert Summitt, Addie M. Swamy-Mruthinti, Satyanarayana Khan, Farooq A. Fujita, Megumi |
| description | A new ion-pair receptor bis(3-bromoindol-2-ylmethyl)(2-pyridylmethyl)amine (
1) was synthesized and studied for its anion and cation binding behavior using ESI-MS and
1H NMR spectroscopy. Among halides,
1 exhibits the strongest binding with Cl
− to form a 1:1 adduct (
K
a
=
1042
±
21 in CD
3CN). Among alkali metal ions, Li
+ and Na
+ showed the strongest binding in the formation of a
1·M
+ complex. The simultaneous binding of Cl
− and Li
+ to
1 was confirmed by
1H NMR titration of a 1:1 mixture of
1 and Cl
− with LiPF
6 in 83:17 v/v mixture of CDCl
3 and DMSO-
d
6. DFT-optimized structures of
1·Cl
−,
1·Li
+, and
1·Li
+·Cl
− are consistent with the chemical shift changes observed in
1H NMR studies. |
| doi_str_mv | 10.1016/j.tetlet.2010.10.012 |
| format | article |
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1) was synthesized and studied for its anion and cation binding behavior using ESI-MS and
1H NMR spectroscopy. Among halides,
1 exhibits the strongest binding with Cl
− to form a 1:1 adduct (
K
a
=
1042
±
21 in CD
3CN). Among alkali metal ions, Li
+ and Na
+ showed the strongest binding in the formation of a
1·M
+ complex. The simultaneous binding of Cl
− and Li
+ to
1 was confirmed by
1H NMR titration of a 1:1 mixture of
1 and Cl
− with LiPF
6 in 83:17 v/v mixture of CDCl
3 and DMSO-
d
6. DFT-optimized structures of
1·Cl
−,
1·Li
+, and
1·Li
+·Cl
− are consistent with the chemical shift changes observed in
1H NMR studies.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2010.10.012</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Alkali metals ; Anion binding ; Anions ; Binding ; Cation binding ; Cations ; ESI-MS ; Indole ; Ion-pair receptor ; NMR spectroscopy ; Nuclear magnetic resonance ; Receptors ; Titration</subject><ispartof>Tetrahedron letters, 2010-12, Vol.51 (50), p.6516-6520</ispartof><rights>2010 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c339t-2e0939a1b86191419a617cbba7bc11eb13fa34e3e96c36ae18d56df56fa640913</citedby><cites>FETCH-LOGICAL-c339t-2e0939a1b86191419a617cbba7bc11eb13fa34e3e96c36ae18d56df56fa640913</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></links><search><creatorcontrib>Skala, Kristin N.</creatorcontrib><creatorcontrib>Perkins, Katelyn G.</creatorcontrib><creatorcontrib>Ali, Amna</creatorcontrib><creatorcontrib>Kutlik, Robert</creatorcontrib><creatorcontrib>Summitt, Addie M.</creatorcontrib><creatorcontrib>Swamy-Mruthinti, Satyanarayana</creatorcontrib><creatorcontrib>Khan, Farooq A.</creatorcontrib><creatorcontrib>Fujita, Megumi</creatorcontrib><title>Anion and cation binding by a new indole/pyridine/amine-based ion-pair receptor</title><title>Tetrahedron letters</title><description>A new ion-pair receptor bis(3-bromoindol-2-ylmethyl)(2-pyridylmethyl)amine (
1) was synthesized and studied for its anion and cation binding behavior using ESI-MS and
1H NMR spectroscopy. Among halides,
1 exhibits the strongest binding with Cl
− to form a 1:1 adduct (
K
a
=
1042
±
21 in CD
3CN). Among alkali metal ions, Li
+ and Na
+ showed the strongest binding in the formation of a
1·M
+ complex. The simultaneous binding of Cl
− and Li
+ to
1 was confirmed by
1H NMR titration of a 1:1 mixture of
1 and Cl
− with LiPF
6 in 83:17 v/v mixture of CDCl
3 and DMSO-
d
6. DFT-optimized structures of
1·Cl
−,
1·Li
+, and
1·Li
+·Cl
− are consistent with the chemical shift changes observed in
1H NMR studies.</description><subject>Alkali metals</subject><subject>Anion binding</subject><subject>Anions</subject><subject>Binding</subject><subject>Cation binding</subject><subject>Cations</subject><subject>ESI-MS</subject><subject>Indole</subject><subject>Ion-pair receptor</subject><subject>NMR spectroscopy</subject><subject>Nuclear magnetic resonance</subject><subject>Receptors</subject><subject>Titration</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNp9UMtOwzAQtBBIlMIfcPCRS1pv7TrxBalCvKRKvcDZsp0NcpUmwXZB_Xscwpk97HNmpB1CboEtgIFc7hcJU4tpsWK_qwWD1RmZQVXygq8rOCczxgQrBOPqklzFuGc5ZMVmZLfpfN9R09XUmTS21ne17z6oPVFDO_ymee5bXA6n4PMBl-aQc2FNxJpmQjEYH2hAh0PqwzW5aEwb8eavzsn70-Pbw0ux3T2_Pmy2heNcpWKFTHFlwFYSFAhQRkLprDWldQBogTeGC-SopOPSIFT1WtbNWjZGCqaAz8ndpDuE_vOIMemDjw7b1nTYH6OGUghZyqyeoWKCutDHGLDRQ_AHE04amB7903s9-adH_8Zt9i_T7ica5je-PAYdncfOYe3zs0nXvf9f4Ad3onrZ</recordid><startdate>20101215</startdate><enddate>20101215</enddate><creator>Skala, Kristin N.</creator><creator>Perkins, Katelyn G.</creator><creator>Ali, Amna</creator><creator>Kutlik, Robert</creator><creator>Summitt, Addie M.</creator><creator>Swamy-Mruthinti, Satyanarayana</creator><creator>Khan, Farooq A.</creator><creator>Fujita, Megumi</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20101215</creationdate><title>Anion and cation binding by a new indole/pyridine/amine-based ion-pair receptor</title><author>Skala, Kristin N. ; Perkins, Katelyn G. ; Ali, Amna ; Kutlik, Robert ; Summitt, Addie M. ; Swamy-Mruthinti, Satyanarayana ; Khan, Farooq A. ; Fujita, Megumi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c339t-2e0939a1b86191419a617cbba7bc11eb13fa34e3e96c36ae18d56df56fa640913</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Alkali metals</topic><topic>Anion binding</topic><topic>Anions</topic><topic>Binding</topic><topic>Cation binding</topic><topic>Cations</topic><topic>ESI-MS</topic><topic>Indole</topic><topic>Ion-pair receptor</topic><topic>NMR spectroscopy</topic><topic>Nuclear magnetic resonance</topic><topic>Receptors</topic><topic>Titration</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Skala, Kristin N.</creatorcontrib><creatorcontrib>Perkins, Katelyn G.</creatorcontrib><creatorcontrib>Ali, Amna</creatorcontrib><creatorcontrib>Kutlik, Robert</creatorcontrib><creatorcontrib>Summitt, Addie M.</creatorcontrib><creatorcontrib>Swamy-Mruthinti, Satyanarayana</creatorcontrib><creatorcontrib>Khan, Farooq A.</creatorcontrib><creatorcontrib>Fujita, Megumi</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Skala, Kristin N.</au><au>Perkins, Katelyn G.</au><au>Ali, Amna</au><au>Kutlik, Robert</au><au>Summitt, Addie M.</au><au>Swamy-Mruthinti, Satyanarayana</au><au>Khan, Farooq A.</au><au>Fujita, Megumi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anion and cation binding by a new indole/pyridine/amine-based ion-pair receptor</atitle><jtitle>Tetrahedron letters</jtitle><date>2010-12-15</date><risdate>2010</risdate><volume>51</volume><issue>50</issue><spage>6516</spage><epage>6520</epage><pages>6516-6520</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>A new ion-pair receptor bis(3-bromoindol-2-ylmethyl)(2-pyridylmethyl)amine (
1) was synthesized and studied for its anion and cation binding behavior using ESI-MS and
1H NMR spectroscopy. Among halides,
1 exhibits the strongest binding with Cl
− to form a 1:1 adduct (
K
a
=
1042
±
21 in CD
3CN). Among alkali metal ions, Li
+ and Na
+ showed the strongest binding in the formation of a
1·M
+ complex. The simultaneous binding of Cl
− and Li
+ to
1 was confirmed by
1H NMR titration of a 1:1 mixture of
1 and Cl
− with LiPF
6 in 83:17 v/v mixture of CDCl
3 and DMSO-
d
6. DFT-optimized structures of
1·Cl
−,
1·Li
+, and
1·Li
+·Cl
− are consistent with the chemical shift changes observed in
1H NMR studies.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2010.10.012</doi><tpages>5</tpages></addata></record> |
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| ispartof | Tetrahedron letters, 2010-12, Vol.51 (50), p.6516-6520 |
| issn | 0040-4039 1873-3581 |
| language | eng |
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| source | ScienceDirect Freedom Collection |
| subjects | Alkali metals Anion binding Anions Binding Cation binding Cations ESI-MS Indole Ion-pair receptor NMR spectroscopy Nuclear magnetic resonance Receptors Titration |
| title | Anion and cation binding by a new indole/pyridine/amine-based ion-pair receptor |
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