A new retention mechanism for an SN2 reaction


Gábor Czakó and his PhD student, István Szabó discovered a new double-inversion mechanism for the F- + CH3Cl SN2 reaction. The theoretical results were published in Nature Communications, one of the best multi-disciplinal scientific journals.
The Walden inversion in a bimolecular nucleophilic substitution (SN2) is one of the best-known stereo-specific reaction mechanisms in organic chemistry. The accurate reaction dynamics simulations revealed a novel reaction path for the F- + CH3Cl SN2 reaction, in which a proton-abstraction-induced inversion is followed by a second inversion, thereby resulting in retention of configuration, as shown in the figure.


The paper, which appeared in January 2015, can be accessed here. Gábor Czakó’s previous work on the reactions of methane and on the modifications of the basic rules of reaction dynamics advocated by the Nobel Prize winner John Polanyi received great international attention and was published in Science and PNAS.