A Study on Restricted Rotation in 1-Acylpyrroles
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概要
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Restricted rotation of the <I>N</I>-acyl group in 1-acylpyrroles was studied by means of NMR spectroscopy. The free energy of activation (<I>ΔF</I><SUB>c</SUB><SUP>\neweq</SUP>) for 1-formylpyrrole is 14.1 kcal/mol, which is less than that for DMF by 6.8 kcal/ mol. The value of <I>ΔF</I><SUB>c</SUB><SUP>\neweq</SUP> decreases in the order 1-formyl-, 1-acetyl-, and 1-benzoyl-pyrrole in exactly the same manner as is found in the series of <I>N</I>,<I>N</I>-dimethylamides with the corresponding acyl group: the difference in <I>ΔF</I><SUB>c</SUB><SUP>\neweq</SUP> between a pair of compounds with the same acyl group in the two series remains constant (<I>ca.</I> 6 kcal/mol). The <I>ΔF</I><SUB>c</SUB><SUP>\neweq</SUP>-value for 3,4-dimethyl-1-acetylpyrrole is larger than that for 1-acetylpyrrole by 1 kcal/mol. In this particular case, the entropy of activation was found to be responsible for the difference in barrier height.
- 公益社団法人 日本化学会の論文
著者
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Matsuo Taku
Department Of Chemical Science And Technology Faculty Of Engineering Kyushu University
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Shosenji Hideto
Department Of Applied Chemistry And Biochemistry Faculty Of Engineering Kumamoto University
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Matsuo Taku
Department of Organic Synthesis, Faculty of Engineering, Kyushu University
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Miyamoto Reiji
Department of Organic Synthesis, Faculty of Engineering, Kyushu University
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Shosenji Hideto
Department of Organic Synthesis, Faculty of Engineering, Kyushu University
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