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| - Modeling SN2 Reactions in Methanol Solution by ab InitioCalculation of Nucleophile Solvent−Substrate Clusters
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| Abstract
| - Ab initio calculations were used to study the SN2 reactions of the CH3OCH2I molecule with amethoxide ion (CH3O-) and a methanol molecule by systematically building up the reaction systemwith explicit incorporation of the methanol solvent molecules. For the reaction of CH3OCH2I witha methoxide ion, the explicit incorporation of the methanol molecules to better solvate the methoxideion led to an increase in the barrier to reaction. For the reaction of CH3OCH2I with a methanolmolecule, the explicit incorporation of the methanol molecules led to a decrease in the barrier toreaction because of an inclination of this reaction to proceed with the nucleophilic displacementsaccompanied by proton transfer through the H-bonding chain. The H-bonding chain served as bothacid and base catalysts for the displacement reaction. A ca. 1015-fold acceleration of the methanoltetramer incorporated SN2 reaction was predicted relative to the corresponding methanol monomerreaction. The properties of the reactions examined are discussed briefly.
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