N-15 NMR and FTIR studies of 2,4-dinitroanilnes and their salts

Twenty-two 2,4-dinitroanilines were synthesised and their pK(a) values were determined. The 2,4-dinitroanilines and their protonated forms were studie d by N-15 NMR spectroscopy. The relations between the N-15 NMR chemical shi fts and the pK(a) values of the 2,4-dinitroanilines and their salts were fo und to be linear. The deprotonation reaction of N-methyl-2,4-dinitroaniline s and N-methyl-2,4,6-trinitroaniline by MTBD was successful only for the la tter and yielded protonated MTBD molecule and the anion in which the electr ons are strongly delocalised. The kinetic parameters of the 2,4-dinitroanil ines in reactions with hydroxide ions in mixed solvent DMSO:water (95:5, v/ v) were determinated and discussed. (C) 2000 Elsevier Science B.V. All righ ts reserved.