Kinetics of the Reaction of Benzyl Bromides with Thiourea

Benzyl Bromide 類와 Thiourea의 反應에 關한 反應速度論的 硏究

  • Yoh, Soo-Dong (Department of Chemistry, Kyungpook National University) ;
  • Lee, Dae-Soo (Department of Chemistry, Kyungpook National University) ;
  • Hong, Soon-Yung (Department of Chemistry, Kyungpook National University)
  • 여수동 (慶北大學校 文理科大學 化學科) ;
  • 이대수 (慶北大學校 文理科大學 化學科) ;
  • 홍순영 (慶北大學校 文理科大學 化學科)
  • Published : 19690900

Abstract

The kinetics of the reaction of m-or p-substituted benzyl bromides with thiourea in methanol at 35.0$^{\circ}$were determined by an electric conductivity method. According to a plot of log k against the Hammett substituent constants, C-Br bond cleavage in benzyl bromide is postulated to be a rate determining step at the SN2 reaction of benzyl bromide with thiourea. Both electron-donating substituents and electron-withdrawing substituents quantitatively affected the rate of reaction, but each in a different manner. A mechanistic possibility was proposed to account for the results. Some activation parameters were also calculated.

Methanol을 溶媒로 한 thiourea와 m- 또는 p- 置換 benzyl bromide 類 와의 反應速度를 電氣傳導度法으로 測定하였다. Hammett 置換基定數와 Log k 와의 關係를 調査한 結果 benzyl bromide에 對한 thiourea의 $SN_2$反應에 있어서 C-Br結合의 解離가 이 反應의 律速段階임을 알 수 있었다. 電子供與基와 電子吸引基는 다같이 反應速度에 定量的인 影響을 주었으나 그 樣式은 서로 달랐다. 이 結果에 符合되는 反應 메카니즘을 考察하였다. 몇 가지 熱力學的 파라미터로 求하였다.

Keywords

References

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