Efficiency of bulky protic solvent for SN2 reaction.

Lee, Sung-Sik; Kim, Ho-Sung; Hwang, Tae-Kyu; Oh, Young-Ho; Park, Sung-Woo; Lee, Sungyul; Lee, Byoung Se; Chi, Dae Yoon

Lee, Sung-Sik; Kim, Ho-Sung; Hwang, Tae-Kyu; Oh, Young-Ho; Park, Sung-Woo; Lee, Sungyul; Lee, Byoung Se; Chi, Dae Yoon.

Affiliation

Lee SS; College of Environmental Science and Applied Chemistry (BK 21), Kyunghee University, Kyungki 446-701, S. Korea.

Org Lett ; 10(1): 61-4, 2008 Jan 03.

Article in En | MEDLINE | ID: mdl-18052384

ABSTRACT

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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Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Year: 2008 Document type: Article

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PubMed Links

Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Year: 2008 Document type: Article