A kinetic investigation of boronic acid/diol interactions and pattern-based recognition of [alpha]-chiral carboxylates

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dc.contributor.advisorAnslyn, Eric V., 1960-en
dc.contributor.committeeMemberIverson, Brent L.en
dc.contributor.committeeMemberCrooks, Richard M.en
dc.contributor.committeeMemberBielawski, Christopher M.en
dc.contributor.committeeMemberKerwin, Seanen
dc.creatorCollins, Byron Ellioten
dc.date.accessioned2010-09-15T20:18:04Zen
dc.date.accessioned2010-09-15T20:19:05Zen
dc.date.accessioned2017-05-11T22:20:12Z
dc.date.available2010-09-15T20:18:04Zen
dc.date.available2010-09-15T20:19:05Zen
dc.date.available2017-05-11T22:20:12Z
dc.date.issued2010-05en
dc.date.submittedMay 2010en
dc.date.updated2010-09-15T20:19:05Zen
dc.descriptiontexten
dc.description.abstractAmine-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.en
dc.format.mimetypeapplication/pdfen
dc.identifier.urihttp://hdl.handle.net/2152/ETD-UT-2010-05-759en
dc.language.isoengen
dc.subjectBoronic aciden
dc.subjectBoronate esteren
dc.subjectBicycloguanidiniumen
dc.titleA kinetic investigation of boronic acid/diol interactions and pattern-based recognition of [alpha]-chiral carboxylatesen
dc.type.genrethesisen

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