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 language | English |
|---|---|
| Pages (from-to) | 12626-12629 |
| Number of pages | 4 |
| Journal | Chemical Communications |
| Volume | 52 |
| Issue number | 85 |
| DOIs | |
| State | Published - 18 Oct 2016 |
Bibliographical note
Publisher Copyright:© 2016 Royal Society of Chemistry.
Funding
This work was inspired by and is dedicated to Meir Lahav, Leslie Leiserowitz and their colleagues. NSERC Canada is thanked for financial support, and LAC acknowledges his membership in the FQRNT supported, multi-university Centre for Self-Assembled Chemical Structures (CSACS). We also thank Prof. Guillaume Lamoureux (Concordia University) for assistance with molecular modeling.
| Funders | Funder number |
|---|---|
| Concordia University |