Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Sn2/E2 Branching in Protic Solvents: A Mechanistic Study

  • Oh, Young-Ho (Department of Applied Chemistry, Kyunghee University) ;
  • Im, Suk (Department of Applied Chemistry, Kyunghee University) ;
  • Park, Sung-Woo (Department of Applied Chemistry, Kyunghee University) ;
  • Lee, Sung-Yul (Department of Applied Chemistry, Kyunghee University) ;
  • Chi, Dae-Yoon (Department of Chemistry, Sogang University)
  • Published : 2009.07.20
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Abstract

We present calculations for $S_N$2/E2 reactions in protic solvents (t-butyl alcohol, ethylene glycol). We focus on the role of the hydroxyl (-OH) groups in determining the $S_N$2/E2 rate constants. We predict that the ion pair E2 mechanism is more favorable than the naked ion E2 reaction in ethylene glycol. E2 barriers are calculated to be much larger (~ 9 kcal/mol) than $S_N$2 reaction barriers in protic solvents, in agreement with the experimental observation [Kim, D. W. et al. J. Am. Chem. Soc. 2006, 128, 16394] of no E2 products in the reaction of CsF in t-butyl alcohol.

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References

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