- MECHANISM OF AMINOMETHANESULFONATE FORMATION AND HYDROLYSIS REACTIONS
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Based on kinetic, structural and synthetic evidence, a mechanism is proposed fro the synthesis of aminomethanesulfonates (R*NH*CHR'*SO3(1-)).The mechanism involves the initial protonation of the amine, proton transfer to the hydroxymethanesulfonate via a six-membered cyclic intermediate followed by a nucleophilic attack of the free amine on the carbon atom.The transition state is assumed to correspond to a structure with practically all the positive charge on the nitrogen atom.For the hydrolysis reaction, the initial protonation of the aminomethanesulfonate is followed by the nucleophilic attack of a water molecule.This mechanism is in agreement with the experimentally determined Hammett reaction constants ρ, i.e. -3.5 for the formation reaction and -2.3 for the hydrolysis.
- Groote, R. A. M. C. De,Neumann, M. G.,Frollini, E.
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p. 295 - 302
(2007/10/02)
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