Nucleophilicity towards a saturated carbon atom: rate constants for the aminolysis of methyl 4-nitrobenzenesulfonate in aqueous solution. A comparison of the n and N+ parameters for amine nucleophilicity

  title={Nucleophilicity towards a saturated carbon atom: rate constants for the aminolysis of methyl 4-nitrobenzenesulfonate in aqueous solution. A comparison of the n and N+ parameters for amine nucleophilicity},
  author={John W. Bunting and Jacqueline M. Mason and Christina K. M. Heo},
  journal={Journal of The Chemical Society-perkin Transactions 1},
Second-order rate constants (kNu) have been measured in aqueous solution (I= 0.1 mol dm –3, 25 °C) for the SN2 reactions of methyl 4-nitrobenzenesulfonate with ammonia, 41 primary amines, 20 secondary amines. 29 tertiary amines and 7 anionic nucleophiles. For the aminolysis reactions, Bronsted-type correlations of nucleophilicity with basicity require the classification of all amines in terms of strictly defined structural classes with βnuc in the range 0.15–0.39. Swain–Scott plots indicate… 
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