Regioselective organocatalysis: a theoretical prediction of the selective rate acceleration of the SN2 reaction between an acetate ion and primary alkyl chlorides in DMSO solution

Organic & Biomolecular Chemistry
J R Pliego

Abstract

High level ab initio calculations, including the solvent effect through a continuum solvation model, predict that 1,4-benzenedimethanol is able to catalyse the S(N)2 reaction between an acetate ion and primary alkyl chlorides in dimethyl sulfoxide solution. The catalysis takes place through two selective hydrogen bonds to the transition state. However, for secondary alkyl chlorides the catalysis is not effective due to steric repulsion and desolvation. This effect induces regioselective control of S(N)2 esterification reactions.

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Citations

Apr 9, 2015·Chemical Reviews·Lung Wa ChungKeiji Morokuma
Oct 30, 2010·Physical Chemistry Chemical Physics : PCCP·Josefredo R Pliego
Dec 17, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Moritz Weiß, Martin Brehm
Mar 24, 2009·The Journal of Physical Chemistry. a·Suk ImDae Yoon Chi
Dec 23, 2008·The Journal of Physical Chemistry. B·Josefredo R Pliego
Feb 3, 2007·The Journal of Physical Chemistry. B·Josefredo R Pliego, Dorila Piló-Veloso
Sep 21, 2007·The Journal of Physical Chemistry. a·Young-Ho OhSungyul Lee

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