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Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy. Differential Rates of N-H Proton-exchange Reactions of Hydrazinecarbothioamide and 4-Methylhydrazinecarbothioamide in Dimethyl Sulfoxide

Yavari, Issa and Roberts, John D. (1980) Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy. Differential Rates of N-H Proton-exchange Reactions of Hydrazinecarbothioamide and 4-Methylhydrazinecarbothioamide in Dimethyl Sulfoxide. Organic Magnetic Resonance, 14 (1). pp. 61-64. ISSN 0030-4921. doi:10.1002/mrc.1270140115. https://resolver.caltech.edu/CaltechAUTHORS:20151006-073241477

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Abstract

The proton-coupled nitrogen-15 NMR spectra of hydrazinecarbothioamide and 4-methylhydrazinecarbothioamide have been taken at the natural-abundance level in neutral, basic and acidic solutions at 25°C. The N-H proton-exchange reactions of the hydrazino-NH_2 groups in both compounds were found to be very rapid in the presence of acid, but quite slow in the presence of base. The hydrazino-NH protons of hydrazinecarbothioamide exhange six times and 200 times faster than the amide protons in the presence of either base or acid, respectively. Similarly, acid- and base-catalyzed N-H proton exchanges of the hydrazino-NH group of 4-methylhydrazinecarbothioamide were found to be two to three orders of magnitude faster than those of N-methylamido protons. These results can be rationalized by consideration of the effect of the lone pair on the hydrazino-NH_2 group on the reactivity of the adjacent -NH- group.


Item Type:Article
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URLURL TypeDescription
http://dx.doi.org/10.1002/mrc.1270140115DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/mrc.1270140115/abstractPublisherArticle
Additional Information:© 1980 Heyden & Son Ltd. Received 18 July 1979; accepted 10 October 1979. Contribution No. 6076. 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 Chemistry6076
Issue or Number:1
DOI:10.1002/mrc.1270140115
Record Number:CaltechAUTHORS:20151006-073241477
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151006-073241477
Official Citation:Yavari, I. and Roberts, J. D. (1980), Nitrogen-15 nuclear magnetic resonance spectroscopy. Differential rates of N[BOND]H proton-exchange reactions of hydrazine-carbothioamide and 4-methylhydrazine-carbothioamide in dimethyl sulfoxide. Org. Magn. Reson., 14: 61–64. doi: 10.1002/mrc.1270140115
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ID Code:60799
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:04 Nov 2015 16:19
Last Modified:10 Nov 2021 22:39

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