Rate-determining carbonyl hydration in the intramolecular hydrolysis of phenacyl phosphonate esters: isotopic probes and activation parameters

IM Kovach, Q Zhao, M Keane…

文献索引：Kovach, Ildiko M.; Zhao, Qinjian; Keane, Matthew; Reyes, Rachel Journal of the American Chemical Society, 1993 , vol. 115, # 23 p. 10471 - 10476

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被引用次数: 10

摘要

Abstract: 4-Nitrophenyl4-substituted-phenacyl methylphosphonate esters (CH3, H, CH30, NOa, and Cl) decompose in aqueous buffers 1-4 orders of magnitude faster than analogs with alkoxy substituents not containing a &carbonyl group. This is consistent with an intramolecular displacement of 4-nitrophenol by the anion of the carbonyl hydrate. 1x0 incorporation into the hydrolysis product of the 4-CH3 derivative from H2180 in alkaline ...