The reaction of 2,4,6-tris(trifluorométhanesulfonyl) anisole with a series of aniline para-X-substituted (X = OCH3, CH3, H, F, Cl) was studied kinetically in the acétonitrile with 20°C. The mechanism and the nature of rate limiting have been proposed. The kinetic findings collected, completed with the analysis of the electronic effects of the substituent X (σ) on the constants of bimolecular rate (k1) have enabled us to establish an excellent correlation of Hammett, with negative ρ value (ρ = -1,82). Besides, good linear relationships was obtained from plots of log k1 against basicity of anilines, with the Brönsted coefficient βNu = 0,41.
N. Elguesmi, R. Goumont, T. Boubaker
SNAr, Brönsted, Hammett