{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/23400"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/23400","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Design, synthesis, and evaluation of conformationally rigid naproxen chiral selectors","abstract":"Conformationally rigid naproxen chiral selector are designed and synthesized based on our chiral recognition hypothesis. When bonded to silica, this type of chiral selectors of rigid conformation are evaluated chromatographically and demonstrate enhanced enantioselectivity towards naproxen and other members of profens, an important group of non-steroidal anti-inflammatory drugs(NSAIDs). The improved enantioselectivity is believed to stem from a highly preorganized disposition of the key functional groups in this type of chiral selectors, which allow for simultaneous optimal use of hydrogen bonding, $\\pi$-$\\pi$ face-to-face and face-to-edge interactions with but one enantiomer of naproxen. Strong support for our chiral recognition model is obtained from systematic chromatographic studies as well as a series of $\\sp1$H$\\{\\sp1\\rm H\\}$ nOe experiments on the 1:1 diastereomeric complexes formed between this type of chiral selector and enantiomers of a naproxen-derived amide.","abstract_html":"Conformationally rigid naproxen chiral selector are designed and synthesized based on our chiral recognition hypothesis. When bonded to silica, this type of chiral selectors of rigid conformation are evaluated chromatographically and demonstrate enhanced enantioselectivity towards naproxen and other members of profens, an important group of non-steroidal anti-inflammatory drugs(NSAIDs). The improved enantioselectivity is believed to stem from a highly preorganized disposition of the key functional groups in this type of chiral selectors, which allow for simultaneous optimal use of hydrogen bonding, <span class=\"etd-inline-math\">&pi;</span>-<span class=\"etd-inline-math\">&pi;</span> face-to-face and face-to-edge interactions with but one enantiomer of naproxen. Strong support for our chiral recognition model is obtained from systematic chromatographic studies as well as a series of $\\sp1$H$\\{\\sp1\\rm H\\}$ nOe experiments on the 1:1 diastereomeric complexes formed between this type of chiral selector and enantiomers of a naproxen-derived amide.","abstract_has_math":true,"creators":["Liu, Yuelong"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Pirkle, William H."],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2011,"date_issued":"2011-05-07T14:12:50Z","date_published":"2011-05-07T14:12:50Z","updated_at":"2026-07-22T22:25:21Z","subjects":["Chemistry, Organic","Chemistry, Pharmaceutical"],"languages":["eng"],"rights":["Copyright 1995 Liu, Yuelong"],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["AAI9543654","(UMI)AAI9543654"],"render_values":[{"text":"AAI9543654","href":null,"code":true},{"text":"(UMI)AAI9543654","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/23400","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Pirkle, William H."]},{"key":"dc:creator","label":"Author","values":["Liu, Yuelong"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2011-05-07T14:12:50Z","10000-01-01","1995"]},{"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","Chemistry, Pharmaceutical"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]},{"key":"dc:rights","label":"Dc Rights","values":["Copyright 1995 Liu, Yuelong"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["AAI9543654","(UMI)AAI9543654","http://hdl.handle.net/2142/23400"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Conformationally rigid naproxen chiral selector are designed and synthesized based on our chiral recognition hypothesis. When bonded to silica, this type of chiral selectors of rigid conformation are evaluated chromatographically and demonstrate enhanced enantioselectivity towards naproxen and other members of profens, an important group of non-steroidal anti-inflammatory drugs(NSAIDs). The improved enantioselectivity is believed to stem from a highly preorganized disposition of the key functional groups in this type of chiral selectors, which allow for simultaneous optimal use of hydrogen bonding, $\\pi$-$\\pi$ face-to-face and face-to-edge interactions with but one enantiomer of naproxen. Strong support for our chiral recognition model is obtained from systematic chromatographic studies as well as a series of $\\sp1$H$\\{\\sp1\\rm H\\}$ nOe experiments on the 1:1 diastereomeric complexes formed between this type of chiral selector and enantiomers of a naproxen-derived amide.","Made available in DSpace on 2011-05-07T14:12:50Z (GMT). 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When bonded to silica, this type of chiral selectors of rigid conformation are evaluated chromatographically and demonstrate enhanced enantioselectivity towards naproxen and other members of profens, an important group of non-steroidal anti-inflammatory drugs(NSAIDs). The improved enantioselectivity is believed to stem from a highly preorganized disposition of the key functional groups in this type of chiral selectors, which allow for simultaneous optimal use of hydrogen bonding, $\\pi$-$\\pi$ face-to-face and face-to-edge interactions with but one enantiomer of naproxen. Strong support for our chiral recognition model is obtained from systematic chromatographic studies as well as a series of $\\sp1$H$\\{\\sp1\\rm H\\}$ nOe experiments on the 1:1 diastereomeric complexes formed between this type of chiral selector and enantiomers of a naproxen-derived amide.","Made available in DSpace on 2011-05-07T14:12:50Z (GMT). No. of bitstreams: 2 license.txt: 4922 bytes, checksum: 910b249b4beec47e7ab768910c8f966f (MD5) 9543654.pdf: 3383671 bytes, checksum: 7b49b320a43bf8c34a6508eae71b4cb2 (MD5) Previous issue date: 1995","Item marked as restricted to the 'UIUC Users [automated]' Group (id=2) by Howard Ding (hding2@illinois.edu) on 2011-05-07T15:04:13Z Item is restricted indefinitely.","Restriction data tranferred 2014-07-01T11:30:40-05:00 Original Data Group with Access UIUC Users [automated] Release Date: none Reason: ETDs are only available to UIUC Users without author permission","ETDs are only available to UIUC Users without author permission","U of I Only"],"dc:identifier":["AAI9543654","(UMI)AAI9543654","http://hdl.handle.net/2142/23400"],"dc:language":["eng"],"dc:rights":["Copyright 1995 Liu, Yuelong"],"dc:subject":["Chemistry, Organic","Chemistry, Pharmaceutical"],"dc:title":["Design, synthesis, and evaluation of conformationally rigid naproxen chiral selectors"],"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":"2026-07-22T22:25:21Z"}