Organochalcogen Substituents in Phenolic Antioxidants

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• 作者：Riccardo Amorati ; Gian Franco Pedulli ; Luca Valgimigli ; Henrik Johansson ; Lars Engman
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：May 21, 2010
• 年：2010
• 卷：12
• 期：10
• 页码：2326-2329
• 全文大小：173K
• 年卷期：v.12,no.10(May 21, 2010)
• ISSN：1523-7052

文摘

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, IR, 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 (3 kcal/mol) to the O−H group.