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

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

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.

Original languageEnglish
Pages (from-to)12626-12629
Number of pages4
JournalChemical Communications
Volume52
Issue number85
DOIs
StatePublished - 18 Oct 2016

Bibliographical note

Publisher Copyright:
© 2016 Royal Society of Chemistry.

Fingerprint

Dive into the research topics of 'Directing the Viedma ripening of ethylenediammonium sulfate using ": Tailor-made " chiral additives'. Together they form a unique fingerprint.

Cite this