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• W2122904053 abstract "The possible catalytic effect of the vicinal hydroxyl group during the ammonolysis of acetylcatechol has been studied by first principle calculations. A very efficient intramolecular catalysis was found to occur when the catechol ester o-OH group is deprotonated: the activation energy of the ammonolysis decreases by 24 kcal mol(-1) as compared to that of acetylphenol ammonolysis. Using this value, the o-oxyanion-catalysed intramolecular ammonolysis was estimated to be orders of magnitude faster than the ammonolysis of acetylphenol or nonionised acetylcatechol. The analogy with the aminolysis of peptidyl-tRNA that occurs during protein biosynthesis implies several orders of magnitude acceleration due to complete or partial deprotonation of its 3'-terminal adenosine 2'-OH providing a mechanistic possibility for general acid-base catalysis by the ribosome." @default.
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• W2122904053 date "2005-01-01" @default.
• W2122904053 modified "2023-09-23" @default.
• W2122904053 title "Theoretical study of the o-OH participation in catechol ester ammonolysis" @default.
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• W2122904053 doi "https://doi.org/10.1039/b417285j" @default.
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