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Nitrogen-15 Magnetic Resonance Spectroscopy XVI—Natural-Abundance Spectra of Aromatic Amines

Lichter, Robert L. and Roberts, John D. (1974) Nitrogen-15 Magnetic Resonance Spectroscopy XVI—Natural-Abundance Spectra of Aromatic Amines. Organic Magnetic Resonance, 6 (12). pp. 636-639. ISSN 0030-4921. https://resolver.caltech.edu/CaltechAUTHORS:20151023-125007229

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Abstract

The ^(15)N chemical shifts of aniline, the toluidines, xylidines, and several halogen and oxygen substituted anilines have been measured at the natural abundance level of ^(15)N. Substituent parameters obtained by multiple regression analysis show that the methyl group induces comparable upfield shifts at the ortho and para positions (2·37 and 2·55 ppm/methyl, respectively) and a small (0·77 ppm/methyl) upfield shift at the meta position. The chemical shifts correlate reasonably well with ^(19)F shifts of similarly substituted fluorobenzenes, with C-1 of the anilines themselves and with Hammett sigma values. While the shifts of C-methyl substituted anilines do not correlate with the methyl resonances of corresponding polymethylbenzenes, those of the halo- and alkoxyanilines show a reasonable parallelism with corresponding ^(13)C-methyl shifts. The results are interpreted in terms of possible modes of transmission of electron density in an alternating and additive manner through the sigma framework.


Item Type:Article
Related URLs:
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http://dx.doi.org/10.1002/mrc.1270061206DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/mrc.1270061206/abstractPublisherArticle
Additional Information:© 1974 Heyden & Son Ltd. Received 24 June 1974; accepted 30 August 1974. Supported by the Public Health Service, Research Grant No. GM-11072, from the Division of General Medical Sciences and by the National Science Foundation. Presented, in part, at the 13th Experimental NMR Conference, Asilomar California, 26th to 30th April l972. Contribution No. 4864.
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U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and Crellin Laboratories of Chemistry4864
Issue or Number:12
Record Number:CaltechAUTHORS:20151023-125007229
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151023-125007229
Official Citation:Lichter, R. L. and Roberts, J. D. (1974), Nitrogen-15 magnetic resonance spectroscopy XVI—natural-abundance spectra of aromatic amines. Org. Magn. Reson., 6: 636–639. doi: 10.1002/mrc.1270061206
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61494
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 21:02
Last Modified:03 Oct 2019 09:08

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