Origin of mysterious alpha effect in nucleophilic substitution reactions unveiled
By 
Fernando Gomollón-Bel2021-06-30T13:31:00
Alpha nucleophiles’ ability to get close to electrophiles – rather than their intramolecular lone pair repulsion – gives them unusual reactivity
The origin of the alpha effect, which gives some nucleophiles unusually high reactivity in substitution reactions, is one of chemistry’s unsolved mysteries. Now, computational chemists have uncovered a largely overlooked mechanism that provides answers to the problem. ‘Our breakthrough was formulating a causal relationship between the electronic structure of the alpha nucleophiles and their intrinsic reactivity,’ says lead researcher Trevor Hamlin from the Vrije University in Amsterdam, the Netherlands.