Amine-functionalized boronic acids have revolutionized the field of carbohydrate sensing in recent years. Capable of rapidly and reversibly forming cyclic boronate esters with of 1,2- and 1,3-diols, polyols, catechols, and α-hydroxycarboxylic acids, boronic acids have found applications spanning from lipid transport to Hydrogen fuel cells. The majority of the work presented in this dissertation will be aimed at gaining a better understanding of the Boron-Nitrogen interactions in ortho-aminomethyl functionalized boronic acids. Chapter 2 will provide an overview of the mechanistic understanding of boronic acid-diol interactions with a special focus on amine-functionalized boronic acids. Chapters 3 – 5 report the progress made by the Anslyn group to develop a more thorough understanding of Boron-Nitrogen interactions and how they affect boronate ester formation. The first introductory chapter will present a the recent advances that have been made in the development of pattern-based sensor systems. Finally, chapter 6 will present the synthesis of a series of bicycloguanidinium hosts, which will be used in a sensing array for chiral carboxylates. / text