Correlation of N.M.R. chemical shifts of amino protons of anilines with Hammett substituent constants

Abstract

The chemical shift of the amino protons in 20 anilines in acetonitrile solution has been correlated with the Hammett constant of the meta or para substituent. The excellent linear correlation for 18 of these anilines has been used to determine the σ^- value for the benzoyl substituent. A less precise linear correlation was observed for the 13 anilines soluble enough to study in carbon tetrachloride solution. A similar relationship can be obtained from deuterochloroform solution spectra.