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Article

Enantiomerization of Axially Chiral Biphenyls: Polarizable MD Simulations in Water and Butylmethylether

1
Department of Computational Biological Chemistry, University of Vienna, Währingerstraße 17, 1090 Vienna, Austria
2
Laboratory of Computational Biology, National Heart, Lung, and Blood Institute (NHLBI), National Institutes of Health (NIH), Bethesda, MD 20892, USA
3
Department of Chemistry, University of South Florida, Tampa, FL 33620, USA
4
Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163, 1060 Vienna, Austria
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2020, 21(17), 6222; https://doi.org/10.3390/ijms21176222
Received: 10 July 2020 / Revised: 20 August 2020 / Accepted: 25 August 2020 / Published: 28 August 2020
In this study, we investigate the influence of chiral and achiral cations on the enantiomerization of biphenylic anions in n-butylmethylether and water. In addition to the impact of the cations and solvent molecules on the free energy profile of rotation, we also explore if chirality transfer between a chiral cation and the biphenylic anion is possible, i.e., if pairing with a chiral cation can energetically favour one conformer of the anion via diastereomeric complex formation. The quantum-mechanical calculations are accompanied by polarizable MD simulations using umbrella sampling to study the impact of solvents of different polarity in more detail. We also discuss how accurate polarizable force fields for biphenylic anions can be constructed from quantum-mechanical reference data. View Full-Text
Keywords: chiral ionic liquids; biphenyl; chirality transfer; molecular dynamics simulations chiral ionic liquids; biphenyl; chirality transfer; molecular dynamics simulations
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MDPI and ACS Style

Zeindlhofer, V.; Hudson, P.; Pálvölgyi, Á.M.; Welsch, M.; Almarashi, M.; Woodcock, H.L.; Brooks, B.; Bica-Schröder, K.; Schröder, C. Enantiomerization of Axially Chiral Biphenyls: Polarizable MD Simulations in Water and Butylmethylether. Int. J. Mol. Sci. 2020, 21, 6222. https://doi.org/10.3390/ijms21176222

AMA Style

Zeindlhofer V, Hudson P, Pálvölgyi ÁM, Welsch M, Almarashi M, Woodcock HL, Brooks B, Bica-Schröder K, Schröder C. Enantiomerization of Axially Chiral Biphenyls: Polarizable MD Simulations in Water and Butylmethylether. International Journal of Molecular Sciences. 2020; 21(17):6222. https://doi.org/10.3390/ijms21176222

Chicago/Turabian Style

Zeindlhofer, Veronika, Phillip Hudson, Ádám M. Pálvölgyi, Matthias Welsch, Mazin Almarashi, H. L. Woodcock, Bernard Brooks, Katharina Bica-Schröder, and Christian Schröder. 2020. "Enantiomerization of Axially Chiral Biphenyls: Polarizable MD Simulations in Water and Butylmethylether" International Journal of Molecular Sciences 21, no. 17: 6222. https://doi.org/10.3390/ijms21176222

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