Dr. Pascal Vermeeren, Dr. Thomas Hansen, Dr. Trevor A. Hamlin, Prof. Dr. F. Matthias Bickelhaupt
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Bimolecular nucleophilic substitution (SN2) and base-induced elimination (E2) generally compete, and it is, therefore, essential to be in control of this competition in synthetic organic chemistry. Herein, we establish guiding principles based on quantitative molecular orbital (MO) theory and the activation strain model to understand and tune the competition between the SN2 and E2 reactions. We discuss the role of key factors, such as the nature of the Lewis base, leaving group, substrate structure, and the solvent. To this end, we introduce the concepts of characteristic distortivity, transition state acidity, intrinsic nucleophilicity, and apparent nucleophilicity. These intuitive concepts equip chemists with conceptual tools to better understand and design reactions for organic synthesis.
期刊介绍：
Chemistry—A European Journal is a truly international journal with top quality contributions (2018 ISI Impact Factor: 5.16). It publishes a wide range of outstanding Reviews, Minireviews, Concepts, Full Papers, and Communications from all areas of chemistry and related fields.
Based in Europe Chemistry—A European Journal provides an excellent platform for increasing the visibility of European chemistry as well as for featuring the best research from authors from around the world.
All manuscripts are peer-reviewed, and electronic processing ensures accurate reproduction of text and data, plus short publication times.
The Concepts section provides nonspecialist readers with a useful conceptual guide to unfamiliar areas and experts with new angles on familiar problems.
Chemistry—A European Journal is published on behalf of ChemPubSoc Europe, a group of 16 national chemical societies from within Europe, and supported by the Asian Chemical Editorial Societies. The ChemPubSoc Europe family comprises: Angewandte Chemie, Chemistry—A European Journal, European Journal of Organic Chemistry, European Journal of Inorganic Chemistry, ChemPhysChem, ChemBioChem, ChemMedChem, ChemCatChem, ChemSusChem, ChemPlusChem, ChemElectroChem, and ChemistryOpen.
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