Journal of the Chemical Society. Perkin transactions II p. 2415 - 2418 (1993)
Update date:2022-08-03
Topics:
Lee, Ikchoon
Lee, Young Sook
Huh, Chul
Lee, Hai Whang
Lee, Byung Choon
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, ρXY, ρYZ and ρXZ, are observed at non-interaction points <*>Z = -0.11 (ρXY = 0), <*>X = -0.02 (ρYZ = 0) and <*>Y = 0.43 (ρXZ = 0) respectively, which have been ascribed to an unusually large third-order cross-interaction constant, ρXYZ = -0.53, for the reaction series.An SN2 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 ρXYZ value.
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