Duthaler, Rudolf O. and Foerster, H. G. and Roberts, John D. (1978) ^(15)N and ^(13)C Nuclear Magnetic Resonance Spectra of Diazo and Diazonium Compounds. Journal of the American Chemical Society, 100 (16). pp. 4974-4979. ISSN 0002-7863. doi:10.1021/ja00484a009. https://resolver.caltech.edu/CaltechAUTHORS:20151007-093104855
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Abstract
Nitrogen-15 and carbon-13 nuclear magnetic resonance (NMR) spectra have been taken of a number of diazo, benzenediazonium, and azido compounds. The ^(13)C chemical shifts of C1 of these substances are at rather high fields (23-112 ppm for diazo compounds compared to 155-185 ppm for imines, and 102-123 ppm for diazonium salts compared to 148 ppm for nitrobenzene) and do not seem explicable in terms of high charge densities on these carbons. The ^(15)N resonances of diazomethane shift downfield when phenyl groups are substituted on carbon and upfield when the carbon is incorporated as C5 of a cyclopentadiene ring. Substitution of electron-donating and electron-attracting groups in the 4 position of benzenediazonium salts shifts the ^(15)N resonances downfield and upfield, respectively.
| Item Type: | Article | |||||||||
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| Alternate Title: | Nitrogen-15 and carbon-13 nuclear magnetic resonance spectra of diazo and diazonium compounds | |||||||||
| Additional Information: | © 1978 American Chemical Society. Received December 12, 1977. Supported by the National Science Foundation, and by the Public Health Service, Research Grant 11072, from the Division of General Medical Sciences; Deutscher Akademischer Austauschdienst NATO Fellow, 1976-1977. We are greatly indebted to Drs. Bruce A. Carlson and Owen Webster, respectively, of the E.I. du Pont de Nemours and Co. for the samples of 2-amino-3,4-dicyanoimidazole and 2,3,4,5-tetracyanodiazocyclopentadiene. | |||||||||
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| Issue or Number: | 16 | |||||||||
| DOI: | 10.1021/ja00484a009 | |||||||||
| Record Number: | CaltechAUTHORS:20151007-093104855 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151007-093104855 | |||||||||
| Official Citation: | Nitrogen-15 and carbon-13 nuclear magnetic resonance spectra of diazo and diazonium compounds Rudolf O. Duthaler, H. G. Foerster, and John D. Roberts Journal of the American Chemical Society 1978 100 (16), 4974-4979 DOI: 10.1021/ja00484a009 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 60868 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 07 Oct 2015 22:51 | |||||||||
| Last Modified: | 10 Nov 2021 22:40 |
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