What Governs the Stereochemistry of the SN2′ Reaction?

✍ Scribed by Borrmann, Tobias ;Stohrer, Wolf-Dieter

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 487 KB
• Volume: 1996
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199619961015

✦ Synopsis

Abstract

Ab initio calculations of negatively charged symmetrical and unsymmetrical transition states of the S~N~2′ reaction indicate that due to electronic reasons and particularly Coulomb interactions the anti transition state is generally more stable than the syn transition state. The experimentally often observed syn preference results mainly from the interaction with a polar solvent and/or the gegenion, which gives rise to higher stabilization of the syn transition state than of the anti transition state.