A CAUTIONARY COMMENT ON A RECENT COMMUNICATION ENTITLED "A MEASURE OF CHARGE TRANSFER (ρ) VERSUS A MEASURE OF BOND TIGHTNESS (ρij) IN THE TRANSITION STATE"

Article abstract of DOI:10.1016/S0040-4039(00)96680-2

We present evidence that the reaction of anilines with ArCH2SO2Cl and ArCH2SO2F goes mainly via the sulfene (ArCH=SO2) and is not a simple nucleophilic displacement at sulfur, as was assumed in the above paper by I.Lee and H.K.Kang (Tetrahedron Lett. 28, 1183 (1987)), and hence that their conclusions about the interpretation of ρ and ρ_XY values are unfounded.