Intramolecular 9-membered hydrogen bonding of 2-arylmethylphenols having carbonyl groups at 2′-position

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• 作者：Yoshimi ; Yasuharu ; Maeda ; Hajime ; Hatanaka ; Minoru ; Mizuno ; Kazuhiko
• 关键词：Intramolecular hydrogen bonding ; 2-Arylmethylphenol ; Variable temperature ¹H NMR ; van't Hoff analysis
• 刊名：Tetrahedron
• 出版年：2004
• 出版时间：October 11, 2004
• 年：2004
• 卷：60
• 期：42
• 页码：9425-9431
• 全文大小：208 K

文摘

Thermodynamic parameters of nine-membered intramolecular hydrogen bonding between carbonyl groups and phenolic hydroxyl groups of 2-arylmethylphenols having methoxycarbonyl, dimethylcarbamoyl, and formyl groups were determined by variable temperature ¹H NMR studies and van't Hoff analysis. The enthalpy of the hydrogen bonding was related to the electron-withdrawing ability of the substituents on the phenol and the basicity of the carbonyl group. The entropy loss of the hydrogen bonding was dependent on the rotation freedom of the phenol group.