Ion-Pair SN2 Reaction of OH and CH3Cl: Activation Strain Analyses of Counterion and Solvent Effects

Jalal Z.A. Laloo, Lydia Rhyman, Olatz Larrañaga, Ponnadurai Ramasami*, F. Matthias Bickelhaupt, Abel de Cózar

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

We have theoretically studied the non-identity SN2 reactions of MnOH(n−1)+CH3Cl (M+=Li+, Na+, K+, and MgCl+; n=0, 1) in the gas phase and in THF solution at the OLYP/6-31++G(d,p) level using polarizable continuum model (PCM) implicit solvation. We want to explore and understand the effect of the metal counterion M+ and solvation on the reaction profile and the stereoselectivity of these processes. To this end, we have explored the potential energy surfaces of the backside (SN2-b) and frontside (SN2-f) pathways. To explain the computed trends, we have carried out analyses with an extended activation strain model (ASM) of chemical reactivity that includes the treatment of solvation effects.

Original languageEnglish
Pages (from-to)1138-1147
Number of pages10
JournalChemistry - An Asian Journal
Volume13
Issue number9
DOIs
Publication statusPublished - 4 May 2018

Keywords

  • activation strain model
  • density functional calculations
  • ion pairs
  • nucleophilic substitution
  • solvent effects

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