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13C NMR study of the substituent effects in ortho-substituted nitrobenzenes

✍ Scribed by Danuta Rasala; Ryszard Gawinecki

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
557 KB
Volume
30
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

^13^C NMR chemical shifts of 22 ortho‐substituted nitrobenzenes are reported. Except for those on C‐3 and C‐5, the effects of the interacting nitro group and the substituent are non‐additive. The chemical shifts of the ipso, ortho and para carbons in the spectra and those of monosubstituted benzenes are linearly dependent. Multiparameter correlation analysis shows a predominant field/inductive effect on the ipso compared with both the ortho and para carbon chemical shifts. It shows that the Reynolds non‐electronic factors evaluate the substituent chemical shifts of the ipso and ortho positions much better than the Charton steric parameters. Moreover, both in ortho‐ and para‐substituted nitrobenzenes the substituent exerts almost the same shift on the ipso carbon atom. This suggests that the studied compounds, except those carrying very bulky groups, show a high tendency to be planar.

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