S<SUB>N</SUB>2 Reactions in Dipolar Aprotic Solvents. Chlorine Isotopic Exchange Reactions of 2-Arylethyl Chlorides, Chloromethyl Aryl Ethers, and Chloromethyl Aryl Sulfides in Acetonitrile

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概要

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• The S<SUB>N</SUB>2 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 10<SUP>5</SUP> times and 10<SUP>3</SUP> times, respectively. Features of the transition states of these S<SUB>N</SUB>2 reactions are discussed.

• 公益社団法人 日本化学会の論文

著者

• Kotani Yasuhiro

  Department of Chemistry, Faculty of Science, Kyoto University

関連論文

• SN2 Reactions in Dipolar Aprotic Solvents. Chlorine Isotopic Exchange Reactions of 2-Arylethyl Chlorides, Chloromethyl Aryl Ethers, and Chloromethyl Aryl Sulfides in Acetonitrile

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