CaltechAUTHORS
  A Caltech Library Service

^(15)N and ^(13)C Nuclear Magnetic Resonance Spectra of Diazo and Diazonium Compounds

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. https://resolver.caltech.edu/CaltechAUTHORS:20151007-093104855

Full text is not posted in this repository. Consult Related URLs below.

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20151007-093104855

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
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja00484a009DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00484a009PublisherArticle
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.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
U.S. Public Health Service (USPHS)GM-11072
Deutscher Akademischer Austauschdienst (DAAD)UNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry5711
Issue or Number:16
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:03 Oct 2019 09:01

Repository Staff Only: item control page