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- W2065376877 abstract "The hydrolysis of coumaran-2-one and 5-substituted 3-phenylcoumaran-2-ones is preceded by a pre-equilibrium involving the formation of an enolate anion at high pH. The pKa of 3-phenylcoumaran-2-one is 8.39 in water at 25 °C and the 3-phenyl substituent increases the carbon acidity by 104. However, despite this ready carbanion formation, the conventional addition–elimination mechanism for hydrolysis of 3-phenylcoumaran-2-ones is confirmed by a solvent kinetic isotope effect of 0.63 and a Brønsted β1g of –0.6. This is compatible with rate limiting formation of a tetrahedral intermediate." @default.
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- W2065376877 date "1998-01-01" @default.
- W2065376877 modified "2023-09-27" @default.
- W2065376877 title "Mechanism of hydrolysis of coumaran-2-ones" @default.
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- W2065376877 doi "https://doi.org/10.1039/a707946j" @default.
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