Nucleophilic Substitution Reactions of Indan-2-yl Arenesulfonates with Anilines in Methanol

Article abstract of DOI:10.1039/P29930002415

The nucleophilic substitution reactions of (Y)-indan-2-yl (Z)-arenesulfonates with (X)-anilines in methanol at 55.0 deg C are reported.Sign reversals in all three second-order cross-interaction constants, ρ_XY, ρ_YZ and ρ_XZ, are observed at non-interaction points <*>_Z = -0.11 (ρ_XY = 0), <*>_X = -0.02 (ρ_YZ = 0) and <*>_Y = 0.43 (ρ_XZ = 0) respectively, which have been ascribed to an unusually large third-order cross-interaction constant, ρ_XYZ = -0.53, for the reaction series.An S_N2 transition state with a tilted, parallel stacked and displaced structure of the three benzene rings in the nucleophile (X), substrate (Y) and leaving group (Z) is proposed to rationalize the strong three-body coupling manifested by the large ρ_XYZ value.

Full text of DOI:10.1039/P29930002415

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