Rotamer populations and molecular structure of 9-isobutyl-1,4-dimethoxytriptvcene: Further evidence for the presence of CH3...O hydrogen bond.
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概要
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<SUP>1</SUP>H NMR spectra of the title compound at low temperatures show the presence of the <I>sc</I> conformer as a major constituent: Δ<I>H</I><SUP>°</SUP>=0.9±0.3 kcal mol<SUP>−1</SUP>, Δ<I>S</I><SUP>°</SUP>=5±2 cal mol<SUP>−1</SUP> for the <I>sc</I>\rightleftarrows<I>ap</I> equilibrium. The line shape analysis of the spectra at various temperatures afforded the following activation parameters for the internal rotation about the C<SUB>9</SUB>–C<SUB><I>i</I>-Bu</SUB> bond: Δ<I>H</I><SUP>\neweq</SUP>=8.8±0.3 kcal mol<SUP>−1</SUP>, Δ<I>S</I><SUP>\neweq</SUP>=−5.0±1.2 cal mol<SUP>−1</SUP> K<SUP>−1</SUP> for the <I>ap</I>→<I>sc</I> process. X-Ray crystallography of the compound revealed that the molecule exists as <I>sc</I> conformers in the crystal. One of the methyl groups of the isobutyl group that directs inward relative to the triptycene skeleton, is placed very closely to the 1-methoxy-oxygen to indicate the presence of the CH<SUB>3</SUB>···O hydrogen bond. Implications of other structural parameters are also discussed.
- 公益社団法人 日本化学会の論文
著者
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Yamamoto Gaku
Department Of Chemistry Faculty Of Science The University Of Tokyo
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Murata Shigeru
Department Of Basic Science Graduate School Of Arts And Sciences The University Of Tokyo
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Oki Michinori
Department Of Chemistry Faculty Of Science Okawama University Of Science
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Toyota Shinji
Department Of Chemistry Faculty Of Science Okawama University Of Science
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Toyota Shinji
Department of Chemistry, Faculty of Science, The University of Tokyo
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Takiguchi Naoyoshi
Department of Chemistry, Faculty of Science, The University of Tokyo
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