Modeling the reactions of 1-naphthylamine and 4-methylaniline with humic acids: Spectroscopic investigations of the covalent linkages

Article abstract of DOI:10.1002/etc.5620130401

The covalent binding of two aromatic amines, 1-naphthylamine and 4- methylaniline, to substituted quinones in aqueous solutions has been studied as a model for the covalent binding of amines to humic acids. An imine compound was the only type of product identified for the reactions between 1- naphthylamine and selected quinones. Reactions of 4-methylaniline with the same quinones gave a 1,4- addition product in addition to the imine compound, although only the imine product was formed when the quinone had bulky substituents at the 2- and 6- positions. These results provide additional insight into the reactions of aromatic amines with humic acid quinones. The covalent binding of two aromatic amines, 1-naphthylamine and 4-methylaniline, to substituted quinones in aqueous solutions has been studied as a model for the covalent binding of amines to humic acids. An imine compound was the only type of product identified for the reactions between 1-naphthylamine and selected quinones. Reactions of 4-methylaniline with the same quinones gave a 1.4- addition product in addition to the imine compound, although only the imine product was formed when the quinone had bulky substituents at the 2- and 6- positions. These results provide additional insight into the reactions of aromatic amines with humic acid quinones.