A phase-transfer catalyst facilitates contact between reactants dissolved in separate, immiscible phases by transferring one reactant species across the phase boundary, thus enhancing the rate of reaction.  A new protocol employing thiolene �click� chemistry allows the synthesis of sulfur-containing quaternary ammonium salts of varied functionalization to form novel phase transfer catalysts.  In this work, reaction rates of second-order nucleophilic substitutions between inorganic salts and organic halides using these catalysts are measured; and their kinetic parameters, including rate constants and activation energies, are evaluated.  The catalytic activities of these novel quaternary ammonium salts are compared to those of their more traditional analogues.  Additionally, the partition coefficients of the catalysts between the aqueous and organic phases are measured, and the influence of the partitioning on the reaction rates is investigated.  The catalytic activity and the partition coefficients are used to evaluate the role of the sulfur in the molecular structure and behavior.

Novel quaternary ammonium salts as phase-transfer catalysts

245th National Meeting (2013)

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