This study focused on the effect different cyclodiaminohexane counterions used with an amino acid-based surfactant undecanoic leucine-valine (und-LeuVal) had on chiral recognition. Counterions varied as configurational isomers (cis vs trans) and constitutional isomers (1,4 or 1,2 cyclodiaminohexane). Enantiomeric separation with Micellar Electrokinetic Chromatography of various binaphthyl derivatives (2,2'-dihydroxy-1,1'-binaphthyl, 1,1'-binaphthyl-2,2'-diyl hydrogen phosphate, and 1,1-Binaphthyl-2,2-diamine) was performed on solutions with various concentrations und-LeuVal and counterion. Previous studies have shown that with increasing pH, fraction of micelle-bonded diamine counterions and micelle radii decrease. In this study, poor to no separation was observed when using either the cis or trans conformation of 1,4-diamine as the counterion. However, 1,2-diamine gives good separation with both cis and trans isomers. When cis-1,2-diamine is used there is an apparent improvement in resolution over the use of the counterion trans-1,2-diamine.

Effect of cyclic diamine isomers on chiral selectivity of amino acid based surfactants

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.