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Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy. Pyridine N-Oxides and Quinoline N-Oxides

Yavari, Issa and Roberts, John D. (1979) Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy. Pyridine N-Oxides and Quinoline N-Oxides. Organic Magnetic Resonance, 12 (2). pp. 87-91. ISSN 0030-4921. http://resolver.caltech.edu/CaltechAUTHORS:20151023-101624042

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Abstract

The noise-decoupled nitrogen-15 NMR spectra of ten pyridine N-oxides and two quinoline N-oxides have been obtained at the natural-abundance level by high-resolution NMR spectroscopy. Substituents at the 4-ring position of pyridine N-oxide, capable of resonance interaction with the N-O moiety, give fairly large shifts in the expected directions. Spectra taken in dimethyl sulfoxide solution give 5–20 ppm and 33–55 ppm downfield shifts with respect to the solutions of the same substances in 2,2,2-trifluoroethanol and trifluoroacetic acid. Solvent influences are discussed in terms of hydrogen bonding and protonation of the N-oxide oxygen. Carbon-13 chemical shifts and one-bond carbon-hydrogen coupling constants of some substituted pyridine N-oxides are reported and discussed.


Item Type:Article
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http://dx.doi.org/10.1002/mrc.1270120209DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/mrc.1270120209/abstractPublisherArticle
Additional Information:© 1979 Heyden & Son Ltd. Received 13 February 1978; accepted 30 March 1978. Supported by the Public Health Service, Research Grant No. GM-11072 from the Division of General Medical Sciences, and by the National Science Foundation.
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U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and Crellin Laboratories of Chemistry5733
Record Number:CaltechAUTHORS:20151023-101624042
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151023-101624042
Official Citation:Yavari, I. and Roberts, J. D. (1979), Nitrogen-15 nuclear magnetic resonance spectroscopy. Pyridine N-oxides and quinoline N-oxides. Org. Magn. Reson., 12: 87–91. doi: 10.1002/mrc.1270120209
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ID Code:61478
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 21:30
Last Modified:26 Oct 2015 21:30

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