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Carbon-13 nuclear magnetic resonance studies of anthraquinones. IV—correlation of substituent effects for 1-substituted anthraquinones

✍ Scribed by Y. Berger; M. Berger-Deguée; A. Castonguay

Publisher
John Wiley and Sons
Year
1981
Tongue
English
Weight
329 KB
Volume
15
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The spectra of various 1‐substituted and 1,5‐disubstituted anthraquinones have been studied and the chemical shifts of the different carbon nuclei determined. The chemical shifts previously reported for 1‐Me‐anthraquinone have been corrected and reassigned. The C‐1, C‐4 and C‐13 shifts of 1‐substituted derivatives are correlated with the chemical shifts of monosubstituted benzenes. Deviations from the regression lines can be explained by the existence of steric factors and hydrogen bonding. A three‐parameter correlation with Swain and Lupton's ℱ and ℛ and Schaefer's Q provides relationships for the prediction of all chemical shifts of 1‐substituted anthraquinones when the substituents have a cylindrical symmetry.

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