EQUILIBRIUM NH ACIDITY OF POLYFLUOROALKYL-CONTAINIG COMPOUNDS
The pK vvalues of NH acids containing a polyfluoroaryl group at the α position to the acid center (polyfluoroalkyl- and diarylamines, polyfluoroanilines) with reference to 9-phenylfluorene were obtained by transmetallation in dimethyl sulfoxide (cation potassium).The acidifying effects of the C6F5, β-C10F7, and C5F4N (tetrafluoro-4-pyridyl) groups were evaluated.The acidity of the C6F5NHR compounds correlates satisfactorily with the parameters of the 19F NMR spectra of the N-anions or NH acids and with the ?* constants of the substituent R.In the series of compounds p-RC6F4NHC6F5 and p-RC6F4NH(O)C6H5 a correlation is observed between the pK values and the Hammett constants of the substituent R.In most cases the conduction of the effect of the substituent R in these series to the NH reaction center is analogous with that in the corresponding unfluorinated series.
Vlasov, V. M.,Terekhova, M. I.,Petrov, E. S.,Shatenshtein, A. I.,Yakobson, G. G.
p. 1807 - 1813
(2007/10/02)
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