791821-94-8Relevant articles and documents
Intramolecular 9-membered hydrogen bonding of 2-arylmethylphenols having carbonyl groups at 2′-position
Yoshimi, Yasuharu,Maeda, Hajime,Hatanaka, Minoru,Mizuno, Kazuhiko
, p. 9425 - 9431 (2007/10/03)
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. The enthalpy of nine-membered intramolecular hydrogen bonding between carbonyl groups and phenolic hydroxyl groups of 2-arylmethylphenols was related to the electron-withdrawing ability of the substituents on the phenol and the basicity of the carbonyl group. The entropy loss was dependent on the rotation freedom of the phenol group.