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Cover Feature: Ion‐Pair S N 2 Reaction of OH − and CH 3 Cl: Activation Strain Analyses of Counterion and Solvent Effects (Chem. Asian J. 9/2018)
Author(s) -
Laloo Jalal Z. A.,
Rhyman Lydia,
Larrañaga Olatz,
Ramasami Ponnadurai,
Bickelhaupt F. Matthias,
de Cózar Abel
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201800314
Subject(s) - sn2 reaction , counterion , chemistry , ion , solvation , strain (injury) , medicinal chemistry , organic chemistry , medicine
Back and forth : OH − is less prone than F − to react via frontside S N 2. It possesses a reactive cone of approach for barrierless substitution at CH 3 Cl via the backside pathway in the gas phase. Solvation in THF further enhances this preference for backside over frontside S N 2 reaction. Yet, OH – can be pushed back to frontside substitution in the ion‐pair S N 2 reaction of MOH+CH 3 Cl for M + =MgCl + . Herein, the physical principles behind this behavior based on quantum chemical activation strain analyses are unveiled. More information can be found in the Full Paper by Ponnadurai Ramasami, F. Matthias Bickelhaupt, Abel de Cózar et al. on page 1138 in Issue 9, 2018 (DOI: 10.1002/asia.201800082).