Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Solvolysis of 2-Phenylethyl Benzenesulfonates in Methanol-Water Mixtures

  • Han, Goang-Lae (Department of Chemistry, Chonbuk National University) ;
  • Park, Jin-Ha (Department of Chemistry, Chonbuk National University) ;
  • Lee, Ik-Choon (Department of Chemistry, Inha University)
  • Published : 1987.10.20
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Abstract

Solvolyses of 2-phenylethyl benzenesulfonates have been studied in methanol-water mixtures. Cross interaction constants, $\rho_{YZ}$, between substituents Y in the substrate and Z in the leaving group indicated somewhat closer distance between the two substituents than expected for the reaction system, which supported the involvment of phenyl group assisted pathway in the solvolysis. A smaller magnitude of $\rho_{YZ}$for MeOH was interpreted as the enhencement of solvent assisted pathway since MeOH is more nucleophilic than $H_2O$. Other selectivity parameters, Winstein coefficient m, Hammett's $\rho_Y^{+_Y}$ and $\rho_Z$, as well as activation parameters supported the participation of aryl assisted and aryl unassisted pathways in the $S_{N^2}$ process of the solvolysis reaction.

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References

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  2. Cross-interaction constants as a measure of the transition state structure. Part 9. The degree of bond formation in theSN2 transition state involving anionic nucleophiles vol.3, pp.8, 1990, https://doi.org/10.1002/poc.610030809
  3. Cross interaction constants as a measure of the transition state structure. 13. Steric effects of theN,N-dimethyl group on the transition state structure in aminolysis of alkyl benzenesulphonates vol.3, pp.11, 1987, https://doi.org/10.1002/poc.610031109
  4. Cross-interaction constants as a measure of the transition state structure. Part 15. Kinetic isotope effects in the SN2 reactions of 2-phenylethyl derivatives with deuterated aniline nucleophiles vol.4, pp.2, 1991, https://doi.org/10.1002/poc.610040206