Inside Back Cover: Ion-Pair SN2 Substitution: Activation Strain Analyses of Counter-Ion and Solvent Effects (Chem. Eur. J. 13/2016)

Backside or frontside attack? It was shown quantum chemically that the comparatively rare front‐side SN2 pathway, leading to retention of the configuration at carbon, can become preferred over the more common back‐side attack that goes with Walden inversion. This change in stereochemistry can be ach...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-03, Vol.22 (13), p.4639-4639
Main Authors: Laloo, Jalal Z. A., Rhyman, Lydia, Ramasami, Ponnadurai, Bickelhaupt, F. Matthias, de Cózar, Abel
Format: Article
Language:English
Subjects:
Activation analysis
Carbon
Chemistry
density functional calculations
Inversion
ion pairs
Physical factors
reaction mechanisms
Retention
solvent effects
Solvents
Stereochemistry
Substitution reactions
transition states
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Summary:Backside or frontside attack? It was shown quantum chemically that the comparatively rare front‐side SN2 pathway, leading to retention of the configuration at carbon, can become preferred over the more common back‐side attack that goes with Walden inversion. This change in stereochemistry can be achieved in the corresponding ion‐pair SN2 process, in which a positive counterion coordinates to the nucleophile and gives a relatively stable cyclic front‐side SN2 transition state. Activation‐strain analyses uncover the physical factors behind such counterions, as well as solvent effects on archetypal substitution reactions. More information can be found in the Full Paper by P. Ramasami, F. M. Bickelhaupt, A. de Cózar et al. on page 4431 ff.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201600643