Payne, Curtis2020-09-082020-09-082020-06https://hdl.handle.net/11299/216120University of Minnesota Ph.D. dissertation. June 2020. Major: Chemistry. Advisor: Steven Kass. 1 computer file (PDF); xx, 500 pages.Hydrogen bonding is a crucial interaction in Nature and plays an important role in the structure and stability of DNA, ion molecular recognition, and the reactivity of enzymes. In the last few decades, synthetic chemists have investigated hydrogen bond donors in the development of metal-free catalysts for a variety of reactions. In these studies, a more acidic species generally results in improved reactivity and stereoselectivity, and a recent investigation uncovered that the acidity of a compound in nonpolar media correlates with its gas phase acidity better than its pKa value in DMSO. As a result, charged hydrogen bond donors and Brønsted acids have been synthesized and are more effective catalysts in nonpolar media compared to their neutral analogues. In this dissertation, this charge enhanced effect is examined through a structure-reactivity relationship and new organocatalytic designs are explored. Additionally, improved analytical methods for the characterization and investigation of these cationic Brønsted acids are discussed.enBrønsted AcidCharge-EnhancedHPLCorganocatalysisThesis or Dissertation