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Nitrogen-15 nuclear magnetic resonance spectroscopy. Effects of hydrogen bonding and protonation on nitrogen chemical shifts in imidazoles

Schuster, Ingeborg I. and Roberts, John D. (1979) Nitrogen-15 nuclear magnetic resonance spectroscopy. Effects of hydrogen bonding and protonation on nitrogen chemical shifts in imidazoles. Journal of Organic Chemistry, 44 (22). pp. 3864-3867. ISSN 0022-3263. http://resolver.caltech.edu/CaltechAUTHORS:20151007-093101318

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Abstract

The ^(15)N chemical shifts of imidazoles, N-methylimidazole and 4-methylimidazole, have been measured in acidic and neutral nonaqueous media. Both hydrogen bonding and protonation of the imidazoles result in upfield shifts of the average of the nitrogen resonances, but the magnitudes of the protonation shifts far exceed those associated with hydrogen bonding. The less-than-normal shifts of the imidazolium ions in nonaqueous media suggest ion-pair formation resulting from interion hydrogen bonding. Such effects diminish in solvents of higher dielectric constant and greater solvating power for salts.


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http://dx.doi.org/10.1021/jo01336a025DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo01336a025PublisherArticle
Additional Information:© 1979 American Chemical Society. Received May 8, 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.
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U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and Crellin Laboratories of Chemistry5813
Record Number:CaltechAUTHORS:20151007-093101318
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151007-093101318
Official Citation:Nitrogen-15 nuclear magnetic resonance spectroscopy. Effects of hydrogen bonding and protonation on nitrogen chemical shifts in imidazoles Ingeborg I. Schuster and John D. Roberts The Journal of Organic Chemistry 1979 44 (22), 3864-3867 DOI: 10.1021/jo01336a025
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60857
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:07 Oct 2015 19:06
Last Modified:07 Oct 2015 19:06

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