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Proximity Effects on Nitrogen-15 Chemical Shifts of 8-Substituted 1-Nitronaphthalenes and 1-Naphthylamines

Schuster, Ingeborg I. and Roberts, John D. (1980) Proximity Effects on Nitrogen-15 Chemical Shifts of 8-Substituted 1-Nitronaphthalenes and 1-Naphthylamines. Journal of Organic Chemistry, 45 (2). pp. 284-287. ISSN 0022-3263. doi:10.1021/jo01290a016. https://resolver.caltech.edu/CaltechAUTHORS:20151007-073141214

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Abstract

^(15)N chemical shifts of several substituted 1-nitronaphthalenes and 8-substituted 1-naphthylamines have been determined and, in general, the substituent effects are unexpectedly small. The high-field shift of the amine nitrogen of 8-nitro-1-aminonaphthalene may indicate a degree of σ complexing between the amino group and the proximate substituents of the type suggested by Dunitz. The smallness of the other substituent effects may be the result of mutual cancellation of opposing larger effects.


Item Type:Article
Related URLs:
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http://dx.doi.org/10.1021/jo01290a016DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo01290a016PublisherArticle
Additional Information:© 1980 American Chemical Society. Received June 4, 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:
Funding AgencyGrant Number
NSFUNSPECIFIED
U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and Crellin Laboratories of Chemistry6041
Issue or Number:2
DOI:10.1021/jo01290a016
Record Number:CaltechAUTHORS:20151007-073141214
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151007-073141214
Official Citation:Proximity effects on nitrogen-15 chemical shifts of 8-substituted 1-nitronaphthalenes and 1-naphthylamines Ingeborg I. Schuster and John D. Roberts The Journal of Organic Chemistry 1980 45 (2), 284-287 DOI: 10.1021/jo01290a016
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60835
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:07 Oct 2015 15:50
Last Modified:10 Nov 2021 22:40

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