Nucleophilic attack by oxyanions on a phosphate monoester dianion: the positive effect of a cationic general Acid.
作者： Anthony J. Kirby , Marcelo F. Lima , Davi da Silva , Faruk Nome
DOI: 10.1021/JA038428W
关键词: Brønsted–Lowry acid–base theory 、 Medicinal chemistry 、 Phosphate 、 Inorganic chemistry 、 Acid catalysis 、 Cationic polymerization 、 Nucleophile 、 Hydrolysis 、 Aryl 、 Fluoride 、 Chemistry
摘要: The two negative charges on a phosphate monoester RO−PO32- at neutral pH provide considerable electrostatic barrier toward reactions with nucleophilic reagents charge the attacking atom. Electrostatic repulsion disappears when hydrolysis of an aryl is catalyzed by neighboring cationic general acid. 8-dimethylammonium-1-phosphate (1) oxyanions, fluoride anion, and hydroxylamines similar rates.
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