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Issue 7, 2018
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High-pressure and temperature dependence of the spontaneous resolution of 1,1′-binaphthyl enantiomers

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Abstract

High pressure increases the temperature of the spontaneous resolution of 1,1′-binaphthyl conformational enantiomers in the crystalline state, which confirms that the enantiomers and racemates are stabilized in the molecular environments in compressed structures. The established pressure–temperature (pT) preference diagram for the racemate–enantiomer spontaneous crystallization corresponds to a boundary between solid phases, as it is consistent with the Clausius–Clapeyron equation, however, the hysteresis of such a solid-state transformation extends to very high pressure, to 3 GPa, at least according to this study. High-pressure X-ray diffraction study on single crystals of 1,1′-binaphthyl racemate and enantiomer reveals their monotonic compression and structural changes up to 3 GPa. It also reveals the increasing role of intermolecular interactions for stabilizing the structures, despite the exceptionally large density difference between the racemate (1.277 g cm−1) and enantiomers (1.183 g cm−1).

Graphical abstract: High-pressure and temperature dependence of the spontaneous resolution of 1,1′-binaphthyl enantiomers

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Article information


Submitted
25 Oct 2017
Accepted
16 Jan 2018
First published
16 Jan 2018

Phys. Chem. Chem. Phys., 2018,20, 5305-5311
Article type
Paper

High-pressure and temperature dependence of the spontaneous resolution of 1,1′-binaphthyl enantiomers

K. Roszak and A. Katrusiak, Phys. Chem. Chem. Phys., 2018, 20, 5305
DOI: 10.1039/C7CP07234A

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