Catalysis and Molecular Recognition: Harnessing Hydrogen Bonds and the Power of Charged Substituents

University of Minnesota Ph.D. dissertation. July 2015. Major: Chemistry. Advisor: Steven Kass. 1 computer file (PDF); xiv, 174 pages.Enzymes employ a variety of approaches to stabilize transition states and facilitate chemical reactions, but none of them are more important than hydrogen bond networks (HBNs) and electrostatic interactions. Herein, hydrogen bonds are studied and exploited. Their strengths are measured in compounds with rigid structures to better understand enzymatic reactions and design stronger organocatalysts. Anion recognition abilities of a series of rigid OH based receptors are also studied to probe the role of hydrogen bonds in anion channels. At the same time, novel strong Br�nsted acids are developed and their catalytic reactivities in different organic reactions are explored. Hydrogen bonding interactions and charged substituents provide a remarkable means for developing novel Br�nsted acid catalysts and new anion receptors