{"id":{"repo_id":"umn","oai_identifier":"oai:conservancy.umn.edu:11299/216120"},"canonical_url":"https://search.dev.ndltd.org/etd/umn/oai:conservancy.umn.edu:11299/216120","repository":{"repo_id":"umn","name":"University of Minnesota","base_url":"https://conservancy.umn.edu/server/oai/request"},"display":{"title":"Charge-Enhanced Brønsted Acids: Catalyst Designs and Analytical Methods","abstract":"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.","abstract_html":"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.","abstract_has_math":false,"creators":["Payne, Curtis"],"institution":null,"degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2020,"date_issued":"2020-06","date_published":"2020-06","updated_at":"2026-07-24T05:19:58Z","subjects":["Brønsted Acid","Charge-Enhanced","HPLC","organocatalysis"],"languages":["en"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/11299/216120","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Payne, Curtis"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2020-09-08T13:57:03Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2020-09-08T13:57:03Z"]},{"key":"dc:date.issued","label":"Date","values":["2020-06"]},{"key":"dc:type","label":"Dc Type","values":["Thesis or Dissertation"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Brønsted Acid","Charge-Enhanced","HPLC","organocatalysis"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["en"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["http://hdl.handle.net/11299/216120"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["University of Minnesota Ph.D. dissertation. June 2020. Major: Chemistry. Advisor: Steven Kass. 1 computer file (PDF); xx, 500 pages."]},{"key":"dc:description.abstract","label":"Abstract","values":["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."]},{"key":"dc:title","label":"Title","values":["Charge-Enhanced Brønsted Acids: Catalyst Designs and Analytical Methods"]}]}],"canonical_facts":{"dc:creator":["Payne, Curtis"],"dc:date.accessioned":["2020-09-08T13:57:03Z"],"dc:date.available":["2020-09-08T13:57:03Z"],"dc:date.issued":["2020-06"],"dc:description":["University of Minnesota Ph.D. dissertation. June 2020. Major: Chemistry. Advisor: Steven Kass. 1 computer file (PDF); xx, 500 pages."],"dc:description.abstract":["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."],"dc:identifier.uri":["http://hdl.handle.net/11299/216120"],"dc:language.iso":["en"],"dc:subject":["Brønsted Acid","Charge-Enhanced","HPLC","organocatalysis"],"dc:title":["Charge-Enhanced Brønsted Acids: Catalyst Designs and Analytical Methods"],"dc:type":["Thesis or Dissertation"]},"updated_at":"2026-07-24T05:19:58Z"}