{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/72297"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/72297","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Synthesis and Complexation Studies of Heterocyclic Compounds With Two or Three Contiguous Hydrogen Bonding Sites","abstract":"The design and synthesis of heterocyclic compounds with two or three adjacent hydrogen bonding sites is described. A general synthetic methodology was developed to produce 5-substituted anthyridine analogs. These compounds exhibited increased stability over the unsubstituted anthyridines. A novel hydrogen bond donor-donor-acceptor (DDA) unit was synthesized to mimic the hydrogen bond functionality of guanosine. A guanosine receptor was developed to ascertain the negative steric interactions inherent in Hamilton's guanosine receptor.","abstract_html":"The design and synthesis of heterocyclic compounds with two or three adjacent hydrogen bonding sites is described. A general synthetic methodology was developed to produce 5-substituted anthyridine analogs. These compounds exhibited increased stability over the unsubstituted anthyridines. A novel hydrogen bond donor-donor-acceptor (DDA) unit was synthesized to mimic the hydrogen bond functionality of guanosine. A guanosine receptor was developed to ascertain the negative steric interactions inherent in Hamilton's guanosine receptor.","abstract_has_math":false,"creators":["Murray, Thomas James"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Zimmerman, Steven C."],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2014,"date_issued":"2014-12-17T21:29:15Z","date_published":"2014-12-17T21:29:15Z","updated_at":"2026-07-22T22:26:06Z","subjects":["Chemistry, Organic"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(UMI)AAI9503280"],"render_values":[{"text":"(UMI)AAI9503280","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/72297","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Zimmerman, Steven C."]},{"key":"dc:creator","label":"Author","values":["Murray, Thomas James"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2014-12-17T21:29:15Z","10000-01-01","1994"]},{"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/2142/72297","(UMI)AAI9503280"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["The design and synthesis of heterocyclic compounds with two or three adjacent hydrogen bonding sites is described. A general synthetic methodology was developed to produce 5-substituted anthyridine analogs. These compounds exhibited increased stability over the unsubstituted anthyridines. A novel hydrogen bond donor-donor-acceptor (DDA) unit was synthesized to mimic the hydrogen bond functionality of guanosine. A guanosine receptor was developed to ascertain the negative steric interactions inherent in Hamilton's guanosine receptor.","New doubly and triply hydrogen bonded complexes with every possible arrangement of hydrogen bond donor (D) and acceptor (A) groups (AD-DA, AA-DD, ADA-DAD, AAD-DDA, AAA-DDD) were studied. The self-association of guanosine was investigated and the resultant dimer was found to favor the Watson-Crick arrangement over the Hoogsteen. Free energies of complexation of doubly hydrogen bonded complexes ranged from 0.4 to 4.7 kcal mol$\\sp{-1}$ while the triply hydrogen bonded complex association energies ranged from 2.4 to 7.0 kcal mol$\\sp{-1}$. The effect of hydrogen bond donors and acceptors that do not participate in primary hydrogen bonds was also examined.","Made available in DSpace on 2014-12-17T21:29:15Z (GMT). No. of bitstreams: 1 9503280.pdf: 6155867 bytes, checksum: 241612e7bd03bf08015406ca0b40d11f (MD5) Previous issue date: 1994","Embargo set by: Seth Robbins for item 72465 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","185 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1994."]},{"key":"dc:title","label":"Title","values":["Synthesis and Complexation Studies of Heterocyclic Compounds With Two or Three Contiguous Hydrogen Bonding Sites"]}]}],"canonical_facts":{"dc:contributor":["Zimmerman, Steven C."],"dc:creator":["Murray, Thomas James"],"dc:date":["2014-12-17T21:29:15Z","10000-01-01","1994"],"dc:description":["The design and synthesis of heterocyclic compounds with two or three adjacent hydrogen bonding sites is described. A general synthetic methodology was developed to produce 5-substituted anthyridine analogs. These compounds exhibited increased stability over the unsubstituted anthyridines. A novel hydrogen bond donor-donor-acceptor (DDA) unit was synthesized to mimic the hydrogen bond functionality of guanosine. A guanosine receptor was developed to ascertain the negative steric interactions inherent in Hamilton's guanosine receptor.","New doubly and triply hydrogen bonded complexes with every possible arrangement of hydrogen bond donor (D) and acceptor (A) groups (AD-DA, AA-DD, ADA-DAD, AAD-DDA, AAA-DDD) were studied. The self-association of guanosine was investigated and the resultant dimer was found to favor the Watson-Crick arrangement over the Hoogsteen. Free energies of complexation of doubly hydrogen bonded complexes ranged from 0.4 to 4.7 kcal mol$\\sp{-1}$ while the triply hydrogen bonded complex association energies ranged from 2.4 to 7.0 kcal mol$\\sp{-1}$. The effect of hydrogen bond donors and acceptors that do not participate in primary hydrogen bonds was also examined.","Made available in DSpace on 2014-12-17T21:29:15Z (GMT). No. of bitstreams: 1 9503280.pdf: 6155867 bytes, checksum: 241612e7bd03bf08015406ca0b40d11f (MD5) Previous issue date: 1994","Embargo set by: Seth Robbins for item 72465 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","185 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1994."],"dc:identifier":["http://hdl.handle.net/2142/72297","(UMI)AAI9503280"],"dc:subject":["Chemistry, Organic"],"dc:title":["Synthesis and Complexation Studies of Heterocyclic Compounds With Two or Three Contiguous Hydrogen Bonding Sites"],"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":"2026-07-22T22:26:06Z"}