Chiral NMR discrimination of amines: Analysis of secondary, tertiary, and prochiral amines using (18-crown-6)-2,3,11,12-tetracarboxylic acid

Enantiomeric discrimination is observed in the 1H and 13C NMR spectra of secondary and tertiary amines in the presence of (−)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid (1). Nonequivalence of the resonances of prochiral nuclei in primary and secondary amines is also observed when they associate wit...

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Veröffentlicht in:	Chirality (New York, N.Y.) N.Y.), 2008-03, Vol.20 (3-4), p.370-378
Hauptverfasser:	Lovely, Ann E., Wenzel, Thomas J.
Format:	Artikel
Sprache:	eng
Schlagworte:	Amines - chemistry chiral discrimination Crown Ethers Magnetic Resonance Spectroscopy - methods NMR prochiral amines secondary amines Stereoisomerism tertiary amines
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creator	Lovely, Ann E. Wenzel, Thomas J.
description	Enantiomeric discrimination is observed in the 1H and 13C NMR spectra of secondary and tertiary amines in the presence of (−)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid (1). Nonequivalence of the resonances of prochiral nuclei in primary and secondary amines is also observed when they associate with 1. The amines are added in their neutral form and are protonated by the carboxylic acid groups of 1 to produce the corresponding ammonium and carboxylate ions. Secondary amines associate with 1 through two hydrogen bonds and an ion pair interaction. Tertiary amines can only form one hydrogen bond to accompany the ion pairing. Chiral discrimination in the 1H and 13C NMR spectra of a series of aryl‐containing secondary amines is of sufficient magnitude to determine enantiomeric purities. The discrimination in the spectra of tertiary amines with 1 is smaller, but 13C NMR spectra provided enough distinction for the determination of enantiomeric purity. Chirality, 2008. © 2007 Wiley‐Liss, Inc.
doi_str_mv	10.1002/chir.20449
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Chirality, 2008. © 2007 Wiley‐Liss, Inc.</description><subject>Amines - chemistry</subject><subject>chiral discrimination</subject><subject>Crown Ethers</subject><subject>Magnetic Resonance Spectroscopy - methods</subject><subject>NMR</subject><subject>prochiral amines</subject><subject>secondary amines</subject><subject>Stereoisomerism</subject><subject>tertiary amines</subject><issn>0899-0042</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kFFPFDEUhRuDgQV58QeYPhE1W7htZ9qpb2SRXQigIRp9a7ptRwuzM9jOBvY_8KPtMiu-8XTvbb5z0nMQekvhkAKwI_s7xEMGRaFeoREtGRDBxc8tNIJKKQJQsB20m9INACjBi220Q6XICxcj9DjJYtPgq8tr7EKyMSxCa_rQtbirscmHT5_wcWuaVQpp_Za87Vpn4mqMex_78LSZ1uG72NnBbJDhZQrtL_yeVsTG7r4l4gNhYz6mdEwZ6X0fjTVx3j2smmCxscG9Qa9r0yS_v5l76Pvp52-TGbn4Mj2bHF8QW3CqiDA5tgUprWOcSyUL6Skw5-talFyAcKqqCmmtqJ2aU2W4dbSsvRe1lcpSvocOBt_85T9Ln3q9yNF905jWd8ukJbCSK8Yy-HEAc4CUoq_1XS4oJ9YU9Lp7vU6sn7rP8LuN63K-8O4_uik7A3QA7kPjVy9Y6cns7PqfKRk0IfX-4Vlj4q0WkstS_7ia6hl8FdPq5FxP-V_7Cp1r</recordid><startdate>200803</startdate><enddate>200803</enddate><creator>Lovely, Ann E.</creator><creator>Wenzel, Thomas J.</creator><general>Wiley Subscription Services, Inc., A Wiley Company</general><scope>BSCLL</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>200803</creationdate><title>Chiral NMR discrimination of amines: Analysis of secondary, tertiary, and prochiral amines using (18-crown-6)-2,3,11,12-tetracarboxylic acid</title><author>Lovely, Ann E. ; Wenzel, Thomas J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4319-6a100c077cd23379747e102deff653606d98847cc6fd9b19a3cd15fee6fc79c13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Amines - chemistry</topic><topic>chiral discrimination</topic><topic>Crown Ethers</topic><topic>Magnetic Resonance Spectroscopy - methods</topic><topic>NMR</topic><topic>prochiral amines</topic><topic>secondary amines</topic><topic>Stereoisomerism</topic><topic>tertiary amines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lovely, Ann E.</creatorcontrib><creatorcontrib>Wenzel, Thomas J.</creatorcontrib><collection>Istex</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>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lovely, Ann E.</au><au>Wenzel, Thomas J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral NMR discrimination of amines: Analysis of secondary, tertiary, and prochiral amines using (18-crown-6)-2,3,11,12-tetracarboxylic acid</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>2008-03</date><risdate>2008</risdate><volume>20</volume><issue>3-4</issue><spage>370</spage><epage>378</epage><pages>370-378</pages><issn>0899-0042</issn><eissn>1520-636X</eissn><abstract>Enantiomeric discrimination is observed in the 1H and 13C NMR spectra of secondary and tertiary amines in the presence of (−)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid (1). Nonequivalence of the resonances of prochiral nuclei in primary and secondary amines is also observed when they associate with 1. The amines are added in their neutral form and are protonated by the carboxylic acid groups of 1 to produce the corresponding ammonium and carboxylate ions. Secondary amines associate with 1 through two hydrogen bonds and an ion pair interaction. Tertiary amines can only form one hydrogen bond to accompany the ion pairing. Chiral discrimination in the 1H and 13C NMR spectra of a series of aryl‐containing secondary amines is of sufficient magnitude to determine enantiomeric purities. The discrimination in the spectra of tertiary amines with 1 is smaller, but 13C NMR spectra provided enough distinction for the determination of enantiomeric purity. 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subjects	Amines - chemistry chiral discrimination Crown Ethers Magnetic Resonance Spectroscopy - methods NMR prochiral amines secondary amines Stereoisomerism tertiary amines
title	Chiral NMR discrimination of amines: Analysis of secondary, tertiary, and prochiral amines using (18-crown-6)-2,3,11,12-tetracarboxylic acid
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