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Intramolecular 9-membered hydrogen bonding of 2-arylmethylphenols having carbonyl groups at 2′-position |
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| Authors: | Yasuharu Yoshimi Minoru Hatanaka |
| Institution: | a Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Fukui University, 3-9-1 Bunkyo, Fukui, Fukui 910-8507, Japan b Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Sakai, Osaka 599-8531, Japan |
| Abstract: | 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. |
| Keywords: | Intramolecular hydrogen bonding 2-Arylmethylphenol Variable temperature 1H NMR van't Hoff analysis |
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