1 Department of Chemistry & Biochemistry, Concordia University, 7141 Sherbrooke Street West, Montréal, Québec H4B 1R6, Canada. Louis.Cuccia@concordia.ca.
2 Bar-Ilan University, Department of Chemistry, Ramat Gan, Israel. Yitzhak.Mastai@biu.ac.il.

Directing the Viedma ripening of ethylenediammonium sulfate using "Tailor-made" chiral additives.

Chem Commun (Camb). 2016 Oct 18;52(85):12626-12629

Authors: Nguyen TP, Cheung PS, Werber L, Gagnon J, Sivakumar R, Lennox C, Sossin A, Mastai Y, Cuccia LA

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.

PMID: 27722259 [PubMed]