^(15)N and ^(13)C Nuclear Magnetic Resonance Spectra of Diazo and Diazonium Compounds
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.
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.Additional details
- Alternative title
- Nitrogen-15 and carbon-13 nuclear magnetic resonance spectra of diazo and diazonium compounds
- Eprint ID
- 60868
- DOI
- 10.1021/ja00484a009
- Resolver ID
- CaltechAUTHORS:20151007-093104855
- NSF
- GM-11072
- U.S. Public Health Service (USPHS)
- Deutscher Akademischer Austauschdienst (DAAD)
- Created
-
2015-10-07Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field
- Other Numbering System Name
- Caltech Gates and Crellin Laboratories of Chemistry
- Other Numbering System Identifier
- 5711