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Nitrogen-15 Magnetic Resonance Spectroscopy. XV. Natural-Abundance Spectra. Chemical Shifts of Hydrazines

Lichter, Robert L. and Roberts, John D. (1972) Nitrogen-15 Magnetic Resonance Spectroscopy. XV. Natural-Abundance Spectra. Chemical Shifts of Hydrazines. Journal of the American Chemical Society, 94 (14). pp. 4904-4906. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151009-133526115

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Abstract

The ^(15)N resonances of the methylhydrazines and some phenylhydrazines have been determined at the natural-abundance level of ^(15)N. The chemical shifts for the methyl compounds were interpretable in terms of deshielding α and β effects. The β shift, -24.4 ppm, is substantially larger than that found for amine ^(15)N (-18.2 ppm) or hydrocarbon nmr resonances (-9.7 ppm), and an explanation is offered in terms of possible steric influences. Although the ^(15)N shifts of the phenylhydrazines also change with structure, the data are so far insufficient to allow derivation of substituent parameters. Nonetheless, the effects of substitution appear to be less systematic than for the alkylhydrazines. The nmr chemical shifts of the methylhydrazines have been measured. While the shifts do not correlate with the ^(15)N shifts, they can be expressed in terms of deshielding β and shielding γ effects comparable to those found for hydrocarbons and alcohols.


Item Type:Article
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http://dx.doi.org/10.1021/ja00769a019DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00769a019PublisherArticle
Additional Information:© 1972 American Chemical Society. Received October 16, 1971. Supported by the Public Health Service, Research Grant No. GM-11072, from the Division of General Medical Sciences, and 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 Chemistry4358
Record Number:CaltechAUTHORS:20151009-133526115
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151009-133526115
Official Citation:Nitrogen-15 magnetic resonance spectroscopy. XV. Natural-abundance spectra. Chemical shifts of hydrazines Robert L. Lichter and John D. Roberts Journal of the American Chemical Society 1972 94 (14), 4904-4906 DOI: 10.1021/ja00769a019
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60955
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:15 Oct 2015 21:52
Last Modified:15 Oct 2015 21:52

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