Transition-state structures for ester aminolysis with and without rate-limiting proton transfer
IM Kovach, M Belz, M Larson, S Rousy…
Index: Kovach, Ildiko M.; Belz, Michael; Larson, Mark; Rousy, Steven; Schowen, Richard L. Journal of the American Chemical Society, 1985 , vol. 107, p. 7360 - 7365
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Citation Number: 26
Abstract
Abstract: The reaction of phenyl acetate (CH3CO2C6H5 and CD3CO2C6H5) with methoxyamine at 25" C in water exhibits 8-secondary deuterium isotope effects k3H/k3D of 0.857 & 0.024 (general-acid catalysis by CH, 02CCH2CH (C02CH3) NH3+, kHOH/kmD= 3.9* 0.8) and 0.867 f 0.009 (general-acid catalysis by CH30NH3+, kHoH/kmo= 1.75 f 0.06). These values are consistent with rate-limiting proton transfer from general acid to a ...
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