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Directing the Viedma Ripening of Ethylenediammonium Sulfate Using "Tailor-made" Chiral Additives

Directing the Viedma Ripening of Ethylenediammonium Sulfate Using "Tailor-made" Chiral Additives

Thi Phuong Thao Nguyen, Pui Shan Monica Cheung, Liora Werber, Jacinthe Gagnon, Reajean Sivakumar, Cameron Lennox, Aaron Sossin, Yitzhak Mastai, Louis A Cuccia

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

PMID: 27722259

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP29841698	(1S,2S)-(−)-1,2-Diphenylethylenediamine		29841-69-8	Price

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