Navigating Past a Fork in the Road: Carbocation-π Interactions Can Manipulate Dynamic Behavior of Reactions Facing Post-Transition-State Bifurcations

Journal of the American Chemical Society
Stephanie R HareDean J Tantillo

Abstract

Dynamics calculations are described for carbocation rearrangements involving product-forming pathways with post-transition-state bifurcations. We show that noncovalent interactions with associated benzene rings (a simple model of aromatic amino acid side chains) can switch inherent dynamical tendencies for competing modes of disrotation, establishing that meaningful changes in dynamically controlled product selectivity can be achieved with few weak noncovalent interactions.

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Citations

Apr 6, 2018·Chemical Science·Florian BartelsMathias Christmann
Sep 22, 2020·Organic & Biomolecular Chemistry·Thomas A Spencer, Robert Ditchfield
Jan 11, 2019·Chemical Science·Stephanie R HareDean J Tantillo
Nov 19, 2020·Physical Chemistry Chemical Physics : PCCP·Yang-Yang XingDean J Tantillo
Jan 27, 2021·Journal of the American Chemical Society·Karen SchrieverPer-Olof Syrén
Feb 11, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Qing SunDean J Tantillo
Mar 12, 2020·Journal of the American Chemical Society·Christina H McCulley, Dean J Tantillo
Dec 7, 2018·Chemical Reviews·Shinji Yamada
Dec 20, 2019·Journal of the American Chemical Society·Vladislav A RoytmanDaniel A Singleton
Jan 10, 2018·The Journal of Physical Chemistry. B·Nilangshu Mandal, Ayan Datta
Feb 9, 2018·Journal of the American Chemical Society·Zhongyue YangK N Houk
Jan 10, 2019·Journal of the American Chemical Society·Xiao-Song XueK N Houk
Nov 28, 2018·Journal of the American Chemical Society·Shuming ChenK N Houk
Jan 6, 2021·Journal of the American Chemical Society·Zhitao Feng, Dean J Tantillo

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