{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/70273"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/70273","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Enantioselective Adsorption of 1,3-Dithiolane-1-Oxides and Related Compounds on Liquid Chromatographic Amino Acid-Derived Chiral Stationary Phases (Resolution, Enantiomers, Sulfoxides)","abstract":"Chiral stationary phases derived from N-3,5-dinitrobenzoyl amino acids such as (R)-phenylglycine, (S)-leucine, (S)-phenylalanine and (S)-valine bonded to aminopropyl silanized silica are employed for preparative and analytical liquid chromatographic separation of the enantiomers of 1,3-dithiolane-1-oxides and related compounds. The structure-enantioselectivity relationships allow determination of two fundamental chiral recognition models for resolution of enantiomeric analytes which, in turn, allow assignment of the absolute configuration of many cyclic sulfoxides on the basis of chromatographic elution order. Confirmation of these assignments is provided by circular dichroism spectroscopy, NMR spectroscopy in the presence of a chiral solvating agent and preparation of chiral sulfoxides from compounds of known absolute configuration. The chiral recognition models are useful for determining the essential functionality required for enantioselective adsorbtion to occur and may be employed for assignment of absolute configuration of many classes of compounds. Lacinilene C and lacinilene C methyl ether are chromatographically resolved and the absolute configurations determined by chromatographic elution order, circular dichroism and NMR spectroscopy in the presence of chiralsolvating agents.","abstract_html":"Chiral stationary phases derived from N-3,5-dinitrobenzoyl amino acids such as (R)-phenylglycine, (S)-leucine, (S)-phenylalanine and (S)-valine bonded to aminopropyl silanized silica are employed for preparative and analytical liquid chromatographic separation of the enantiomers of 1,3-dithiolane-1-oxides and related compounds. The structure-enantioselectivity relationships allow determination of two fundamental chiral recognition models for resolution of enantiomeric analytes which, in turn, allow assignment of the absolute configuration of many cyclic sulfoxides on the basis of chromatographic elution order. Confirmation of these assignments is provided by circular dichroism spectroscopy, NMR spectroscopy in the presence of a chiral solvating agent and preparation of chiral sulfoxides from compounds of known absolute configuration. The chiral recognition models are useful for determining the essential functionality required for enantioselective adsorbtion to occur and may be employed for assignment of absolute configuration of many classes of compounds. Lacinilene C and lacinilene C methyl ether are chromatographically resolved and the absolute configurations determined by chromatographic elution order, circular dichroism and NMR spectroscopy in the presence of chiralsolvating agents.","abstract_has_math":false,"creators":["Hamper, Bruce Cameron"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2014,"date_issued":"2014-12-15T23:18:18Z","date_published":"2014-12-15T23:18:18Z","updated_at":"2026-07-22T22:26:02Z","subjects":["Chemistry, Organic"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(UMI)AAI8502162"],"render_values":[{"text":"(UMI)AAI8502162","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/70273","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Hamper, Bruce Cameron"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2014-12-15T23:18:18Z","10000-01-01","1984"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry, Organic"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/70273","(UMI)AAI8502162"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Chiral stationary phases derived from N-3,5-dinitrobenzoyl amino acids such as (R)-phenylglycine, (S)-leucine, (S)-phenylalanine and (S)-valine bonded to aminopropyl silanized silica are employed for preparative and analytical liquid chromatographic separation of the enantiomers of 1,3-dithiolane-1-oxides and related compounds. The structure-enantioselectivity relationships allow determination of two fundamental chiral recognition models for resolution of enantiomeric analytes which, in turn, allow assignment of the absolute configuration of many cyclic sulfoxides on the basis of chromatographic elution order. Confirmation of these assignments is provided by circular dichroism spectroscopy, NMR spectroscopy in the presence of a chiral solvating agent and preparation of chiral sulfoxides from compounds of known absolute configuration. The chiral recognition models are useful for determining the essential functionality required for enantioselective adsorbtion to occur and may be employed for assignment of absolute configuration of many classes of compounds. Lacinilene C and lacinilene C methyl ether are chromatographically resolved and the absolute configurations determined by chromatographic elution order, circular dichroism and NMR spectroscopy in the presence of chiralsolvating agents.","Made available in DSpace on 2014-12-15T23:18:18Z (GMT). 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The structure-enantioselectivity relationships allow determination of two fundamental chiral recognition models for resolution of enantiomeric analytes which, in turn, allow assignment of the absolute configuration of many cyclic sulfoxides on the basis of chromatographic elution order. Confirmation of these assignments is provided by circular dichroism spectroscopy, NMR spectroscopy in the presence of a chiral solvating agent and preparation of chiral sulfoxides from compounds of known absolute configuration. The chiral recognition models are useful for determining the essential functionality required for enantioselective adsorbtion to occur and may be employed for assignment of absolute configuration of many classes of compounds. Lacinilene C and lacinilene C methyl ether are chromatographically resolved and the absolute configurations determined by chromatographic elution order, circular dichroism and NMR spectroscopy in the presence of chiralsolvating agents.","Made available in DSpace on 2014-12-15T23:18:18Z (GMT). No. of bitstreams: 1 8502162.pdf: 5855517 bytes, checksum: eb9fad0a8ab862ffdffa8b0c8b662921 (MD5) Previous issue date: 1984","Embargo set by: Seth Robbins for item 70439 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","U of I Only","197 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1984."],"dc:identifier":["http://hdl.handle.net/2142/70273","(UMI)AAI8502162"],"dc:subject":["Chemistry, Organic"],"dc:title":["Enantioselective Adsorption of 1,3-Dithiolane-1-Oxides and Related Compounds on Liquid Chromatographic Amino Acid-Derived Chiral Stationary Phases (Resolution, Enantiomers, Sulfoxides)"],"dc:type":["text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Ph.D."],"thesis:institution_name":["University of Illinois at Urbana-Champaign"]},"updated_at":"2026-07-22T22:26:02Z"}