Kinetics of the Reaction of Substituted Pyridines with Benzyl Benzenesulfonate (Ⅴ)

Benzyl Benzenesulfonate 와 置換피리딘類의 反應에 關한 反應速度論的 硏究 (第5報).

  • Woo Bung Lee (Department of Chemistry, Techer's College, Kyungpook National University) ;
  • Soo Dong Yoh (Department of Chemistry, Techer's College, Kyungpook National University) ;
  • Soon Yung Hong (Department of Chemistry, Hanyang University)
  • 이우붕 (慶北大學校 師範大學 化學科) ;
  • 여수동 (慶北大學校 師範大學 化學科) ;
  • 홍순영 (漢陽大學校 文理科大學 化學科)
  • Published : 19770230

Abstract

The rate constant of the reaction of 3-or 4-substituted pyridines with benzyl benzenesulfonate in acetone at $35^{\circ}C$ were determined by an electric conductivity method. According to the Hammett plot, the rates were increased the electron donating ability at the $S_N2$ reaction of benzyl benzenesulfonate with pyridine and 4-$NH_2$ pyridine was correlated with ${\sigma}^+$ than Hammett ${\sigma}$ value. This result was explained that $NH_2$ group and N atom in pyridine are largely contribute by resonance. In Br$\"{o}$nsted plot, 4-amino and electron attracting group were deviated from the increasing part at linearity. It was considered to solvent effects on substituents. A mechanistic possibility was proposed to account for the results. Some activation parameters were also calculated.

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References

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