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Nitrogen-15 nuclear magnetic resonance studies of benzenediazonium ions. Effects of solvent, substituent, anion, and 18-crown-6

Casewit, Carla and Roberts, John D. and Bartsch, Richard A. (1982) Nitrogen-15 nuclear magnetic resonance studies of benzenediazonium ions. Effects of solvent, substituent, anion, and 18-crown-6. Journal of Organic Chemistry, 47 (15). pp. 2875-2878. ISSN 0022-3263. http://resolver.caltech.edu/CaltechAUTHORS:20151005-113555474

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Abstract

Effects of solvent change on the ^(15)N resonance positions for p-n-butylbenzenediazonium tetrafluoroborate are small. In contrast, the influence of substituents on the ^(15)N chemical shifts for para-substituted benzenediazonium tetrafluoroboratea in acetonitrile are relatively large. For the p-n-butylbenzenediazonium cation in dichloromethane, replacement of the tetrafluoroborate anion by chloride produces small downfield shifts of the ^(15)N resonance positions for both nitrogens. Complexation of benzenediazonium tetrafluoroborates by 18-crown-6 in N,V-dimethylformamide induces relatively large changes in the ^(15)N chemical shifts. Attempts to detect crown ether complexation of other species with diazonium-like termini by ^(15)N NMR were unsuccessful.


Item Type:Article
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http://dx.doi.org/10.1021/jo00136a012DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo00136a012UNSPECIFIEDArticle
Additional Information:© 1982 American Chemical Society. Received December 1, 1981. Supported by the National Science Foundation. (b) IBM Graduate Fellow, 1979-1980.
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IBM Graduate FellowUNSPECIFIED
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Caltech Gates and Crellin Laboratories6379
Record Number:CaltechAUTHORS:20151005-113555474
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151005-113555474
Official Citation:Nitrogen-15 nuclear magnetic resonance studies of benzenediazonium ions. Effects of solvent, substituent, anion, and 18-crown-6 Carla Casewit, John D. Roberts, and Richard A. Bartsch The Journal of Organic Chemistry 1982 47 (15), 2875-2878 DOI: 10.1021/jo00136a012
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60760
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:05 Oct 2015 21:50
Last Modified:05 Oct 2015 21:50

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