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Chiral Recognition by ^(15)N NMR Spectroscopy. 8-Benzyl-5,6,7,8-tetrahydroquinoline

Dyllick-Brenzinger, Rainer and Roberts, John D. (1980) Chiral Recognition by ^(15)N NMR Spectroscopy. 8-Benzyl-5,6,7,8-tetrahydroquinoline. Journal of the American Chemical Society, 102 (3). pp. 1166-1167. ISSN 0002-7863. doi:10.1021/ja00523a045. https://resolver.caltech.edu/CaltechAUTHORS:20151007-073139909

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Abstract

Chiral recognition through diastereomeric complex formation with optically active solvents or solutes and detected by chemical-shift differences in ^1H or ^(19)FNMR spectroscopy has many applications, including for the determination of absolute configurations. The NMR shift differences observed in many chiral recognition experiments are not large and, because the reported changes of ^(15)N chemical shifts of pyridine-type nitrogens on hydrogen-bond formation and protonation are, respectively, usually 15-30 and ~100 ppm, it seemed possible that differential complexation between an optically active proton donor and the separate enantiomers of chiral pyridine derivatives might lead to substantial ^(15)N chemical-shift differences.


Item Type:Article
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http://dx.doi.org/10.1021/ja00523a045DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00523a045PublisherArticle
Alternate Title:Chiral recognition by nitrogen-15 NMR spectroscopy. 8-Benzyl-5,6,7,8-tetrahydroquinoline
Additional Information:© 1980 American Chemical Society. Received August 20, 1979. Supported by the National Science Foundation and by the Public Health Service, Research Grant No. GM-11072 from the Division of General Medical Sciences.
Funders:
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U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and Crellin Laboratories of Chemistry6098
Issue or Number:3
DOI:10.1021/ja00523a045
Record Number:CaltechAUTHORS:20151007-073139909
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151007-073139909
Official Citation:Chiral recognition by nitrogen-15 NMR spectroscopy. 8-Benzyl-5,6,7,8-tetrahydroquinoline Rainer Dyllick-Brenzinger and John D. Roberts Journal of the American Chemical Society 1980 102 (3), 1166-1167 DOI: 10.1021/ja00523a045
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60831
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:07 Oct 2015 15:07
Last Modified:10 Nov 2021 22:40

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