Collect. Czech. Chem. Commun. 1991, 56, 368-385
https://doi.org/10.1135/cccc19910368

Carbon-13 substituent-induced chemical shifts in benzene derivatives: Substituted anilines

Miloš Buděšínskýa, Dan Johnelsb, Ulf Edlundb and Otto Exnera

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia
b Department of Organic Chemistry, University of Umeå, S-901 87 Umeå, Sweden

Abstract

Carbon-13 NMR spectra are reported for 59 meta- and para-substituted anilines in deuterochloroform or in its mixture with hexadeuterodimethyl sulphoxide. The substituent-induced chemical shifts (SCS) of ring carbon atoms in position 4 correlate well with dual substituent parameters (DSP). In the remaining positions correlations are not satisfactory with any kind of known substituent constants. There is, however, a close resemblance between SCS in the same position of meta- and para-substituted anilines and even in other series of aromatic compounds.