Argentation chromatography is a powerful separation technique for selectively targeting the subtle differences existing among carbon-carbon double bonds in unsaturated organic compounds (e.g. degree of unsaturation, cis/trans configuration, double bond position, etc.). Traditionally, argentation chromatography is performed by depositing silver nitrate onto a silica gel surface (SiO2 + AgNO3) or by utilizing a strong cation exchange phase to immobilize a silver-ion. These silver-ion chromatography techniques have proven themselves invaluable over the past five decades across numerous fields and applications where small, but significant differences in unsaturation predominate in the molecules of interest. Despite the uniquely high olefin selectively exhibited by silver-ion modified phases, this technique remains notoriously difficult to implement in a consistent and reliable manner. Major issues in phase stability such as light sensitivity, silver leeching and low compound recovery have largely prevented silver-ion chromatography from becoming a more widely adopted separation technique. Recent advancements in argentation chromatography by the Huang group at Brown University have demonstrated silica gel functionalized with a silver(I)-thiolate moiety effectively eliminates all major drawbacks associated with silver-ion chromatography, while still retaining high olefin selectivity during liquid chromatography separations. We present recent developments in the applications of these silver(I)-thiolate stationary phases in addition to some fundamental insights into the retention mechanism controlling separation and the contribution different types of olefins have on overall retention.

Towards the next generation of argentation liquid chromatography for olefin selective separations

247th National Meeting (2014)

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