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3‐[4′‐(Diethylboryl)phenyl]pyridine: Exclusive Crystallization of the Cyclic Tetramer
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- Shigeharu Wakabayashi
- Department of Clinical Nutrition Faculty of Health Science Suzuka University of Medical Science Suzuka Mie 510-0293 Japan
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- Natsu Sugiyama
- Department of Clinical Nutrition Faculty of Health Science Suzuka University of Medical Science Suzuka Mie 510-0293 Japan
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- Yasuhiro Ohki
- Department of Chemistry Graduate School of Science Nagoya University Chikusa-ku Nagoya 464-8602 Japan
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- Takahito Itoh
- Department of Chemistry for Materials Graduate School of Engineering Mie University Tsu Mie 514-8507 Japan
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- Toshikazu Kitagawa
- Department of Chemistry for Materials Graduate School of Engineering Mie University Tsu Mie 514-8507 Japan
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Description
<jats:title>Abstract</jats:title><jats:p>The crystallization of 3‐[4′‐(diethylboryl)phenyl]pyridine (<jats:bold>1</jats:bold>), which formed a mixture of oligomers in solution with the cyclic trimer as a major component, in acetone at 0 °C afforded a cyclic tetramer that co‐crystallized with solvent molecules. Similarly, solutions of compound <jats:bold>1</jats:bold> in toluene at 10 °C and in benzene at 8 °C furnished the cyclic tetramer with the incorporation of toluene and benzene molecules, respectively, thus suggesting that the cyclic tetramer was the minor component. <jats:sup>13</jats:sup>C CP/MAS NMR spectroscopy of precipitates of compound <jats:bold>1</jats:bold> suggested that precipitation from acetone and toluene each afforded mixtures of the cyclic trimer and the cyclic tetramer, whereas precipitation from benzene exclusively furnished the cyclic tetramer. Therefore, it appeared that crystallization readily shifted the equilibrium towards the cyclic tetramer in benzene. The thermodynamic parameters for the equilibrium between these two oligomers in [D<jats:sub>6</jats:sub>]benzene, as determined from a van′t Hoff plot, were Δ<jats:italic>H</jats:italic>°=−8.8 kcal mol<jats:sup>−1</jats:sup> and Δ<jats:italic>S</jats:italic>°=−23.7 cal mol<jats:sup>−1</jats:sup> K<jats:sup>−1</jats:sup>, which were coincident with previously reported calculations and observations.</jats:p>
Journal
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- Chemistry – An Asian Journal
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Chemistry – An Asian Journal 14 (4), 568-573, 2019-01-25
Wiley