Rate-equilibrium relationships for reactions of families of carbanion nucleophiles with N-benzyl-N, N-dimethylanilinium cations and with alkyl chlorides, bromides, and …

FG Bordwell, DL Hughes

Index: Bordwell, Frederick G.; Hughes, David L. Journal of the American Chemical Society, 1986 , vol. 108, # 23 p. 7300 - 7309

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Citation Number: 27

Abstract

Abstract: Rates of reaction of a family of 9-methylfluorenide anions, 9-MeFI-, with 15 substituted N-benzyl-N, N-dimethylanilinium cations, GC6H4CH2N (Me) 2C6H4Y+, were measured in a 0.8 M KN03 solution of MezSO at 25 OC. Substitution in the benzyl moiety produced a U-shaped Hammett plot, with m-CN reacting 9-to 15-fold faster than H and p- Me0 reacting 1.5-to 3-fold faster than H, depending on the basicity of the 9-RFI-ion. ...