Nucleophilic Substitution Reactions of Benzyl Bromides and Benzyl Iodide with Anilines in MeOH-MeCN Mixtures

MeOH-MeCN 혼합용매계에서 브롬화벤질 및 요오드화벤질과 아닐린 사이의 친핵성 치환반응

  • 이익춘 (인하대학교 이과대학 화학과) ;
  • 손세철 (인하대학교 이과대학 화학과) ;
  • 송호봉 (경기대학교 이과대학 화학과) ;
  • 이병춘 (충북대학교 사범대학 과학교육과)
  • Published : 1984.06.20


Kinetic studies for the nucleophilic substitution reactions of para-substituted benzyl bromides and benzyl iodide with anilines were carried out in MeOH-MeCN mixtures at 35.0$^{\circ}$C. Hammett $ {\rho}_N,\;{\rho}_C$, Bronsted $ {\beta}$ and solvatochromic correlation coefficient a, s values were determined in order to clarify the transition state variations caused by changing nucleophiles, substituents, leaving group and solvents. The results of solvatochromic equation showed that ${\pi}^{ast}$effect was a dominant factor for the reaction systems studied. It was shown that the reaction proceeds via the dissociative $S_N$2 mechanism using the potential energy surface model approach. The potential energy surface model approach however failed to account for the transition state variation due to leaving group changes. The quatum mechanical approach showed that kinetic results were consistent with proposed dissociative $S_N$2 mechanism.



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