Directing the Viedma ripening of ethylenediammonium sulfate using “Tailor-made” chiral additives†,10.1039/C6CC06534A

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

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

Chemical Communications Pub Date : 09/26/2016 00:00:00 , DOI:10.1039/C6CC06534A

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.