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

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.

Name thesis:degree_name

Doctor of Philosophy

Level thesis:degree_level

Doctoral

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Texas at Austin

Year dc:date.issued

2010

Author dc:creator

• Collins, Byron Elliot

Advisor dc:contributor.advisor

• Anslyn, Eric V., 1960-

Committee members dc:contributor.committeemember

• Iverson, Brent L.
• Crooks, Richard M.
• Bielawski, Christopher M.
• Kerwin, Sean

• Boronic acid
• Boronate ester
• Bicycloguanidinium

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/2152/ETD-UT-2010-05-759

OAI identifier oai:identifier

oai:repositories.lib.utexas.edu:2152/ETD-UT-2010-05-759