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

Schuster, Ingeborg I. and Dyllick-Brenzinger, Christina and Roberts, John D. (1979) Nitrogen-15 nuclear magnetic resonance spectroscopy. Effects of hydrogen bonding and protonation on nitrogen chemical shifts of pyrazoles. Journal of Organic Chemistry, 44 (11). pp. 1765-1768. ISSN 0022-3263. http://resolver.caltech.edu/CaltechAUTHORS:20151007-093102214

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Abstract

The ^(15)N chemical shifts of pyrazole, N-methylpyrazole, 3-methyl- and 3,5-dimethylpyrazoles, and indazole have been measured as a function of solvent and acidity of the medium. Hydrogen bonding and protonation result in upfield shifts of both the pyridine- and pyrrole-type nitrogen resonances of these substances with the effect being larger a t the pyridine-type nitrogens. The protonation shifts far exceed those resulting from hydrogen bonding.


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http://dx.doi.org/10.1021/jo01325a003DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo01325a003PublisherArticle
Additional Information:© 1979 American Chemical Society. Received September 5, 1978. 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 Chemistry5874
Record Number:CaltechAUTHORS:20151007-093102214
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151007-093102214
Official Citation:Nitrogen-15 nuclear magnetic resonance spectroscopy. Effects of hydrogen bonding and protonation on nitrogen chemical shifts of pyrazoles Ingeborg I. Schuster, Christina Dyllick-Brenzinger, and John D. Roberts The Journal of Organic Chemistry 1979 44 (11), 1765-1768 DOI: 10.1021/jo01325a003
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60859
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:07 Oct 2015 22:30
Last Modified:07 Oct 2015 22:30

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