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Inside Back Cover: Origin of the α‐Effect in S N 2 Reactions (Angew. Chem. Int. Ed. 38/2021)
Author(s) -
Hansen Thomas,
Vermeeren Pascal,
Bickelhaupt F. Matthias,
Hamlin Trevor A.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202108477
Subject(s) - nucleophile , reactivity (psychology) , sn2 reaction , pauli exclusion principle , chemistry , hydroxide , substrate (aquarium) , homo/lumo , cover (algebra) , stereochemistry , catalysis , physics , organic chemistry , molecule , condensed matter physics , medicine , alternative medicine , oceanography , pathology , geology , mechanical engineering , engineering
The α ‐effect is a “reactivity booster” that affords the less basic peroxide (HOO − ) the edge over hydroxide (HO − ) in the Grand Prix of S N 2 Reactivity. In their Research Article on page 20840, Trevor A. Hamlin and co‐workers equip researchers with two criteria that α‐nucleophiles need to fulfill to exhibit an α‐effect: (i) a small HOMO lobe on the nucleophilic center, to reduce the destabilizing Pauli repulsion with the substrate; and (ii) a high‐energy HOMO to overcome the loss of favorable orbital overlap with the substrate.