2007•Organic LettersRequires access

Efficiency of Bulky Protic Solvent for SN2 Reaction

Sung-Sik Lee, Hosung Kim, Tae-Kyu Hwang, Young‐Ho Oh, Sungwoo Park, Sungyul Lee, Byoung Se Lee, Dae Yoon Chi

Abstract

We calculate and compare the effects of aprotic vs protic solvent on the rate of SN2 reaction [F- + C3H7OMs--> C3H7F + OMs-]. We find that aprotic solvent acetonitrile is more efficient than a small protic solvent such as methanol. Bulky protic solvent (tert-butyl alcohol) is predicted to be quite efficient, giving the rate constant that is similar to that in CH3CN. Our calculated relative activation barriers of the SN2 reaction in methanol, tert-butyl alcohol, and CH3CN are in good agreement with experimental observations.

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Key concepts: Chemistry, Solvent, Combinatorial chemistry, Organic chemistry, Medicinal chemistry