Issue 85, 2016

Directing the Viedma ripening of ethylenediammonium sulfate using “Tailor-made” chiral additives

Abstract

Both enantiomers of trans-cyclohexane-1,2-diammonium sulfate and trans-1,2-diphenylethylenediammonium sulfate were used as “tailor-made” additives to direct the mirror-symmetry breaking in the attrition-enhanced deracemization (i.e. Viedma ripening) of conglomerate crystals of ethylenediammonium sulfate (EDS). Isothermal titration calorimetry (ITC) shows chiral recognition of (1R,2R)- and (1S,2S)-1,2-diphenylethylenediamine to EDS crystals where the enthalpy of adsorption of the (1R,2R)-isomer on L-EDS crystals is higher in comparison to that on D-EDS crystals. These results are consistent with a “rule of reversal” mechanism driving the chiral outcome of the Viedma ripening of EDS.

Graphical abstract: Directing the Viedma ripening of ethylenediammonium sulfate using “Tailor-made” chiral additives

Supplementary files

Article information

Article type
Communication
Submitted
08 Mha 2016
Accepted
26 Ndz 2016
First published
26 Ndz 2016

Chem. Commun., 2016,52, 12626-12629

Directing the Viedma ripening of ethylenediammonium sulfate using “Tailor-made” chiral additives

T. P. T. Nguyen, P. S. M. Cheung, L. Werber, J. Gagnon, R. Sivakumar, C. Lennox, A. Sossin, Y. Mastai and L. A. Cuccia, Chem. Commun., 2016, 52, 12626 DOI: 10.1039/C6CC06534A

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