Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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The Effect of Alkali Metal Ions on Nucleophilic Substitution Reactions of Aryl 2-Furoates with Alkali Metal Ethoxides in Ethanol

  • Dong-Sook Kwon (Department of Chemistry, Ewha Womans University) ;
  • Jung-Hyun Nahm (Department of Chemistry, Ewha Womans University) ;
  • Ik-Hwan Um (Department of Chemistry, Ewha Womans University)
  • Published : 1994.08.20
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Abstract

Rate constants have been measured spectrophotometrically for the nucleophilic substitution reactions of p-and m-nitrophenyl 2-furoates (4 and 5, respectively) with alkali metal ethoxides ($EtO^-M^+$) in absolute ethanol at 25$^{\circ}$C. The reactivity of $EtO^-M^+$ toward 4 is in the order $EtO^-K^+$ > $EtO^-Na^+$> $EtO^-Li^+$ > $EtO^-K^+$+ 18-crown-6 ether. This is further confirmed by an ion pairing treatment method. The present result indicates that (1) ion paired $EtO^-M^+$ is more reactive than dissociated $EtO^-$ ; (2) the alkali metal ions ($K^+,\;Na^+,\;Li^+$) behave as a catalyst; (3) the catalytic effect increases with increasing the size of the metal ion. A similar result has been obtained for the reaction of 5, however, the catalytic effects shown by the metal ions are more significant in the reaction of 5 than in that of 4.

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References

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