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http://dx.doi.org/10.5012/bkcs.2009.30.7.1535

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)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.7, 2009 , pp. 1535-1538 More about this Journal
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.
Keywords
$S_{n}2$/E2 branching; Protic solvent;
Citations & Related Records
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