Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Structure-Reactivity Relationship of Benzyl Benzenesulfonates. Part 4. Application of Correlation Interaction Coefficients

  • Published : 1998.04.20
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Abstract

The mechanism of nucleophilic displacement was studied by using three variable systems of ${\rho}_X,\; {\rho}_Y,\; and {\rho}_Z$ obtained from the change of substituent X, Y, and Z for the reaction of (Z)-substituted benzyl (X)-benzensulfonates with (Y)-substituted thiobenzamides in acetone at 45 ℃. The results ${\rho}_Z$<0 and ${\rho}_YZ$>${\rho}_XZ$ indicate that this reaction series proceeded via a dissociative $S_N2$ mechanism. The prediction of the movement of TS by using the sign of ${\rho}_XZ{\cdot}{\rho}_{YZ}$ accorded with the Hammond postulate.

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References

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