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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 7
BKCSDE 30(7)
July 20, 2009 

SN2/E2 Branching in Protic Solvents: A Mechanistic Study
Young Ho Oh, Suk Im, Sung Woo Park, Sungyul Lee*, Dae Yoon Chi*
SN2/E2 branching, Protic solvent
We present calculations for SN2/E2 reactions in protic solvents (t-butyl alcohol, ethylene glycol). We focus on the role of the hydroxyl (-OH) groups in determining the SN2/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 SN2 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.
1535 - 1538
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