Organochalcogen Substituents in Phenolic Antioxidants

被引：57

作者：

Amorati, Riccardo ^{[1
]}

Pedulli, Gian Franco ^{[1
]}

Valgimigli, Luca ^{[1
]}

Johansson, Henrik ^{[2
]}

Engman, Lars ^{[2
]}

机构：

[1] Univ Bologna, Dept Organ Chem A Mangini, I-40126 Bologna, Italy

[2] Uppsala Univ, Dept Biochem & Organ Chem, SE-75123 Uppsala, Sweden

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 10期

基金：

瑞典研究理事会;

关键词：

CHAIN-BREAKING; PRINCIPLES; ABILITY; PROFILE; SULFUR;

D O I：

10.1021/ol100683u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Little is known about the ED/EW character of organochalcogen substituents and their contribution to the O-H bond dissociation enthalpy (BDE) in phenolic compounds. A series of ortho- and para-(S,Se,Te)R-substituted phenols were prepared and investigated by EPR, IA, and computational methods. Substituents lowered the O-H BDE by >3 kcal/mol in the para position, while the ortho-effect was modest due to hydrogen bonding (similar to 3 kcal/mol) to the O-H group.

引用

页码：2326 / 2329

页数：4