SN2 Reactions in Dipolar Aprotic Solvents. Chlorine Isotopic Exchange Reactions of 2-Arylethyl Chlorides, Chloromethyl Aryl Ethers, and Chloromethyl Aryl Sulfides in Acetonitrile
- 1 November 1971
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 44 (11), 3091-3095
- https://doi.org/10.1246/bcsj.44.3091
Abstract
The SN2 reactions having a symmetrical transition state were studied in a dipolar aprotic solvent. A good Hammett correlation was found for the chlorine isotopic exchange reactions in acetonitrile between tetraethylammonium chloride and three types of substituted methyl chlorides, 2-arylethyl chlorides, chloromethyl aryl ethers, and chloromethyl aryl sulfides. The reaction constant was positive for 2-arylethyl chlorides and negative for the methyl chlorides possessing an α-heteroatom. The presence of oxygen and sulfur atom on the α-position to the reaction center resulted in a rate enhancement of about 105 times and 103 times, respectively. Features of the transition states of these SN2 reactions are discussed.Keywords
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