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

被引：9
|
作者：
Yoshimi, Y
Maeda, H
Hatanaka, M
Mizuno, K
机构：
[1] Osaka Prefecture Univ, Grad Sch Engn, Dept Appl Chem, Sakai, Osaka 5998531, Japan
[2] Univ Fukui, Fac Engn, Dept Appl Chem & Biotechnol, Fukui 9108507, Japan
来源：
TETRAHEDRON | 2004年 / 60卷 / 42期
关键词：
intramolecular hydrogen bonding; 2-arylmethylphenol; variable temperature H-1 NMR; van't Hoff analysis;
D O I：
10.1016/j.tet.2004.08.007
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 H-1 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. (C) 2004 Elsevier Ltd. All rights reserved.
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页码：9425 / 9431
页数：7
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