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19F nmr spectra of mesomeric carbanions generated from polyfluorodiarylacetonitriles. The electronic effect of perfluoroalkyl groups
Authors:VM Vlasov  OV Zakharova  GG Yakobson
Institution:Institute of organic Chemistry, Siberian Division of the Academy of Sciences, 630090 Novosibirsk U.S.S.R.
Abstract:19F NMR spectra of 1,2- dimethoxyethane solutions of Na- and Li- salts of polyfluorinated carbanions p - RC6F4C(CN)C6F4R′-p] Na+ (Li+) and of their neutral precursors p-RC6F4CH(CN)C6F4R′-p / R  F or CF3 and R′= CF3, CF2CF3, CF(CF3)2 and C(CF3)3/ have been studied. The values of changes in the chemical shifts of fluorine atoms in the ring and the side chain are practically the same when going from the precursor to carbanion with the perfluoroalkyl group being varied. This gave grounds to conclude that the electronic effect of the perfluoroalkyl groups is rather similar. The 19F NMR method has revealed no differences in the predominant mechanism of the negative charge distribution by these groups.
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