Imaging dynamic fingerprints of competing E2 and SN2 reactions

Eduardo Carrascosa, Jennifer Meyer, Jiaxu Zhang, Martin Stei, Tim Michaelsen, William L. Hase, Li Yang and Roland Wester ()
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Eduardo Carrascosa: Universität Innsbruck
Jennifer Meyer: Universität Innsbruck
Jiaxu Zhang: Harbin Institute of Technology
Martin Stei: Universität Innsbruck
Tim Michaelsen: Universität Innsbruck
William L. Hase: Texas Tech University
Li Yang: Harbin Institute of Technology
Roland Wester: Universität Innsbruck

Nature Communications, 2017, vol. 8, issue 1, 1-7

Abstract: Abstract The competition between bimolecular nucleophilic substitution and base-induced elimination is of fundamental importance for the synthesis of pure samples in organic chemistry. Many factors that influence this competition have been identified over the years, but the underlying atomistic dynamics have remained difficult to observe. We present product velocity distributions for a series of reactive collisions of the type X− + RY with X and Y denoting the halogen atoms fluorine, chlorine and iodine. By increasing the size of the residue R from methyl to tert-butyl in several steps, we find that the dynamics drastically change from backward to dominant forward scattering of the leaving ion relative to the reactant RY velocity. This characteristic fingerprint is also confirmed by direct dynamics simulations for ethyl as residue and attributed to the dynamics of elimination reactions. This work opens the door to a detailed atomistic understanding of transformation reactions in even larger systems.

Date: 2017
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DOI: 10.1038/s41467-017-00065-x

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