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Nitrogen-15 Nuclear Magnetic Resonance. Structure of Sulfaguanidine

Sullivan, Glenn R. and Roberts, John D. (1977) Nitrogen-15 Nuclear Magnetic Resonance. Structure of Sulfaguanidine. Journal of Organic Chemistry, 42 (6). pp. 1095-1096. ISSN 0022-3263. http://resolver.caltech.edu/CaltechAUTHORS:20151008-115811733

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Abstract

Sulfaguanidine (1) is unusual compared to the many derivatives of sulfanilamide (4-aminobenzenesulfonamide) that contain the grouping -SO_2HN- in being insoluble in aqueous alkali. Its 4-amino group is comparably basic to the other sulfanilamides (pK_B = 11.25) but its guanidino group is only very weakly basic (pK_B = 13.52). The nonacidic character of the compound caused Schwenker to investigate its infrared and ^lH NMR spectra and, by comparison of the infrared spectra in KBr pellets with those of several model compounds, it appeared that 1 had no infrared absorption which could be ascribed to the N-H bond of an -SO_2NH- group. The ^1H NMR spectrum in dimethyl sulfoxide solution was less decisive because of serious overlap of the downfield N-H resonances with the resonances of the aromatic ring, but nonetheless, there appeared to be no evidence for the three different kinds of -SO_2NHC(=NH)NH_2 proton resonances predicted for the conventional guanidine structure. It was concluded therefore that the correct structure for sulfaguanidine is not 1a, but instead the tautomer 1b. Schwenker's work seems to have been largely, if not totally, ignored, and as recently as 1975, a ^(13)C investigation formulates sulfaguanidine as 1a in accord with the standard reference works.


Item Type:Article
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http://dx.doi.org/10.1021/jo00426a041DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo00426a041PublisherArticle
Additional Information:© 1977 American Chemical Society. Received August 16, 1976. Supported by the Public Health Service, Research Grant 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 Chemistry5155
Record Number:CaltechAUTHORS:20151008-115811733
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151008-115811733
Official Citation:Nitrogen-15 nuclear magnetic resonance. Structure of sulfaguanidine Glenn R. Sullivan and John D. Roberts The Journal of Organic Chemistry 1977 42 (6), 1095-1096 DOI: 10.1021/jo00426a041
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60913
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:11 Oct 2015 11:16
Last Modified:11 Oct 2015 11:16

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