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Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy. Differential Rates of N-H Proton-Transfer Reactions in Phenylhydrazine

Yavari, Issa and Roberts, John D. (1978) Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy. Differential Rates of N-H Proton-Transfer Reactions in Phenylhydrazine. Journal of the American Chemical Society, 100 (15). pp. 4662-4664. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20151008-070942295

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Abstract

High-resolution proton-coupled ^(15)N NMR spectra of neat phenylhydrazine (1) have been studied at the natural abundance level over the temperature range of 20-70 ºC. Proton transfer from the -NH_2 group was found to be about two orders of magnitude faster than that from the -NH- group. The ^(15)N chemical shifts of 1 in a variety of basic, neutral, and acidic solvents show that influences of the medium are different for the two types of nitrogens in 1. Proton-coupled ^(15)N spectra of 1 in various solvents confirm the results of the variable-temperature studies. The differential rates of the proton-transfer reactions of 1 can be ascribed to two different bimolecular exchange mechanisms.


Item Type:Article
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http://dx.doi.org/10.1021/ja00483a004DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00483a004PublisherArticle
Alternate Title:Nitrogen-15 nuclear magnetic resonance spectroscopy. Differential rates of nitrogen-hydrogen proton-transfer reactions in phenylhydrazine
Additional Information:© 1978 American Chemical Society. Received December 12, 1977. July 19, 1978. Supported by the National Science Foundation, and by the Public Health Service, Research Grant GM-11073 from the Division of General Medical Sciences.
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U.S. Public Health Service (USPHS)GM-11073
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Caltech Gates and Crellin Laboratories of Chemistry5710
Issue or Number:15
Record Number:CaltechAUTHORS:20151008-070942295
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151008-070942295
Official Citation:Nitrogen-15 nuclear magnetic resonance spectroscopy. Differential rates of nitrogen-hydrogen proton-transfer reactions in phenylhydrazine Issa Yavari and John D. Roberts Journal of the American Chemical Society 1978 100 (15), 4662-4664 DOI: 10.1021/ja00483a004
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60883
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:08 Oct 2015 17:59
Last Modified:03 Oct 2019 09:01

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