RESUMEN
Directed chiral symmetry breaking and asymmetric amplification of ethylenediammonium sulfate in the presence of chiral amino acids was achieved using an abrasion/grinding method.
Asunto(s)
Aminoácidos/química , Compuestos de Amonio Cuaternario/química , Cristalización , Modelos Moleculares , EstereoisomerismoRESUMEN
Complete asymmetric amplification of ethylenediammonium sulfate was achieved under continuous dissolution/crystallization conditions using an abrasion/grinding method.
Asunto(s)
Etilenodiaminas/química , Compuestos de Amonio Cuaternario/síntesis química , Ácidos Sulfúricos/química , Fenómenos Químicos , Química Física , Cristalización , Enlace de Hidrógeno , Modelos Moleculares , Presión , Compuestos de Amonio Cuaternario/química , Solubilidad , Estrés Mecánico , Factores de TiempoRESUMEN
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.