Effect of Solvation on the Menschutkin Reaction in Liquid Sulfur Dioxide

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概要

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• 1) The effect of the solvent solvation has been compared in the reaction between methyliodide and various bases in liquid sulfur dioxide, methanol and nitrobenzene. The reaction rate in liquid sulfur dioxide is very much depressed, and the differences in the relative rates among bases are reduced in sulfurdioxide (a leveling effect) as compared to the other two solvents.<BR>2) The order of the relative rates is reversed in liquid sulfur dioxide; pyridine>triethylamine ><I>N</I>,<I>N</I>-dimethylaniline><I>N</I>,<I>N</I>-dimethylbenzylamine, whereas in methanol and in nitrobenzene, <I>N</I>,<I>N</I>-dimethylbenzylamine is the fastest of the bases. The reasons for this have been discussed.<BR>3) The effect of the <I>o</I>-methyl substituent of the bases on the reaction rate has been examined. In liquid sulfur dioxide, the rate ratios <I>k</I><SUB><I>o</I>－Me</SUB>⁄<I>k</I><SUB>H</SUB> are again leveling, while in methanol the ratios are differentiating. The solvation of sulfur dioxide has been considered to be the reason.<BR>4) An isokinetic relation between <I>ΔE</I><SUP>\neweq</SUP> and <I>ΔS</I><SUP>\neweq</SUP> has been observed, and the isokinetic temperature calculated as 350°K; however, no linear dependence was obtained between <I>ΔE</I><SUP>\neweq</SUP><SUB><I>o</I>－Me</SUB>–<I>ΔE</I><SUP>\neweq</SUP><SUB>H</SUB> and <I>ΔH</I><SUB>p</SUB>–<I>ΔH</I><SUB>o</SUB>.

• 社団法人 日本化学会の論文

著者

• Tokura N.

  The Chemical Research Institute of Non-Aqueous Solutions

• Kondo Yasuhiko

  The Chemical Research Institute of Non-Aqueous Solutions Tohoku University

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• The Cationic Copolymerization of Styrene and p-Brornostyrene in Liquid Sulfur Dioxide
• The Beckmann Rearrangement of 1,2-Cyclohexane-dione Dioxime in Liquid Sulfur Dioxide
• The Reactions of 1, 2-Cyclopentanedione Dioxime and of 1, 2, 3-and 1,3,5-Cyclohexanetrione Trioximes in Liquid Sulfur Dioxide
• The Menschutkin Reaction in Liquid Sulfur Dioxide
• Solvent Effect on the Rearrangement of Cyclohexanoneoxime-p-toluenesulfonate. The Ionizing Power of Liquid Sulfur Dioxide
• The Reaction of Isobutene with Chloromethyl Methyl Ether in Liquid Sulfur Dioxide
• Effect of Solvation on the Menschutkin Reaction in Liquid Sulfur Dioxide

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