{"id":{"repo_id":"york","oai_identifier":"oai:yorkspace.library.yorku.ca:10315/27605"},"canonical_url":"https://search.dev.ndltd.org/etd/york/oai:yorkspace.library.yorku.ca:10315/27605","repository":{"repo_id":"york","name":"York University","base_url":"https://yorkspace.library.yorku.ca/oai/request"},"display":{"title":"Synthesis of Electron Deficient N-heterocyclic-carbenes and Activity of Imidazol-2-imine Thioureate Ligand on Group 10 Transition Metals","abstract":"Previous work in the Lavoie group has resulted in the synthesis of new imidazol-2-imine ligands that have low activity towards ethylene polymerization due to their electron rich nature. In an attempt to alleviate this an electron poor naphthalene-1,4-dione-IMes imidazol-2-imine ligand (L) was synthesized in 90% yield (14a) and coordinated to titanium (LTiCpCl2, 15). The resulting complex successfully polymerizes ethylene at a rate of 75 kg PE mol catalyst–1 h–1. A separate study focused on the coordination of functionalized imidazol-2-imine thioureate ligands (L’) to late transition metal. Three complexes were synthesized. Ni(methylallyl)L’ (7), Pd(allyl)L’ (8), and NiL’2 (9) were isolated in 85, 85, and 61% yields, respectively and all spectroscopically characterized. The X-ray crystallographic structure of 9 shows the unexpected N^S binding mode for the ligand. Complexes 7 and 8 have sparing activity towards ethylene polymerization, neither having productivity above 2 kg PE mol–1 h–1.","abstract_html":"Previous work in the Lavoie group has resulted in the synthesis of new imidazol-2-imine ligands that have low activity towards ethylene polymerization due to their electron rich nature. In an attempt to alleviate this an electron poor naphthalene-1,4-dione-IMes imidazol-2-imine ligand (L) was synthesized in 90% yield (14a) and coordinated to titanium (LTiCpCl2, 15). The resulting complex successfully polymerizes ethylene at a rate of 75 kg PE mol catalyst–1 h–1. A separate study focused on the coordination of functionalized imidazol-2-imine thioureate ligands (L’) to late transition metal. Three complexes were synthesized. Ni(methylallyl)L’ (7), Pd(allyl)L’ (8), and NiL’2 (9) were isolated in 85, 85, and 61% yields, respectively and all spectroscopically characterized. The X-ray crystallographic structure of 9 shows the unexpected N^S binding mode for the ligand. Complexes 7 and 8 have sparing activity towards ethylene polymerization, neither having productivity above 2 kg PE mol–1 h–1.","abstract_has_math":false,"creators":["Harkness, Michael Byron"],"institution":null,"degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":["Lavoie, Gino G"],"committee_chairs":[],"committee_members":[],"year":2014,"date_issued":"2014-07-09","date_published":"2014-07-09","updated_at":"2026-07-24T06:33:34Z","subjects":["Inorganic chemistry"],"languages":["en"],"rights":["Author owns copyright, except where explicitly noted. Please contact the author directly with licensing requests."],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/10315/27605","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Lavoie, Gino G"]},{"key":"dc:creator","label":"Author","values":["Harkness, Michael Byron"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2014-07-11T18:19:25Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2014-07-11T18:19:25Z"]},{"key":"dc:date.issued","label":"Date","values":["2014-07-09"]},{"key":"dc:type","label":"Dc Type","values":["Electronic Thesis or Dissertation"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Inorganic chemistry"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["en"]},{"key":"dc:rights","label":"Dc Rights","values":["Author owns copyright, except where explicitly noted. Please contact the author directly with licensing requests."]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["http://hdl.handle.net/10315/27605"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Previous work in the Lavoie group has resulted in the synthesis of new imidazol-2-imine ligands that have low activity towards ethylene polymerization due to their electron rich nature. In an attempt to alleviate this an electron poor naphthalene-1,4-dione-IMes imidazol-2-imine ligand (L) was synthesized in 90% yield (14a) and coordinated to titanium (LTiCpCl2, 15). The resulting complex successfully polymerizes ethylene at a rate of 75 kg PE mol catalyst–1 h–1. A separate study focused on the coordination of functionalized imidazol-2-imine thioureate ligands (L’) to late transition metal. Three complexes were synthesized. Ni(methylallyl)L’ (7), Pd(allyl)L’ (8), and NiL’2 (9) were isolated in 85, 85, and 61% yields, respectively and all spectroscopically characterized. The X-ray crystallographic structure of 9 shows the unexpected N^S binding mode for the ligand. Complexes 7 and 8 have sparing activity towards ethylene polymerization, neither having productivity above 2 kg PE mol–1 h–1."]},{"key":"dc:title","label":"Title","values":["Synthesis of Electron Deficient N-heterocyclic-carbenes and Activity of Imidazol-2-imine Thioureate Ligand on Group 10 Transition Metals"]}]}],"canonical_facts":{"dc:contributor.advisor":["Lavoie, Gino G"],"dc:creator":["Harkness, Michael Byron"],"dc:date.accessioned":["2014-07-11T18:19:25Z"],"dc:date.available":["2014-07-11T18:19:25Z"],"dc:date.issued":["2014-07-09"],"dc:description.abstract":["Previous work in the Lavoie group has resulted in the synthesis of new imidazol-2-imine ligands that have low activity towards ethylene polymerization due to their electron rich nature. In an attempt to alleviate this an electron poor naphthalene-1,4-dione-IMes imidazol-2-imine ligand (L) was synthesized in 90% yield (14a) and coordinated to titanium (LTiCpCl2, 15). The resulting complex successfully polymerizes ethylene at a rate of 75 kg PE mol catalyst–1 h–1. A separate study focused on the coordination of functionalized imidazol-2-imine thioureate ligands (L’) to late transition metal. Three complexes were synthesized. Ni(methylallyl)L’ (7), Pd(allyl)L’ (8), and NiL’2 (9) were isolated in 85, 85, and 61% yields, respectively and all spectroscopically characterized. The X-ray crystallographic structure of 9 shows the unexpected N^S binding mode for the ligand. Complexes 7 and 8 have sparing activity towards ethylene polymerization, neither having productivity above 2 kg PE mol–1 h–1."],"dc:identifier.uri":["http://hdl.handle.net/10315/27605"],"dc:language.iso":["en"],"dc:rights":["Author owns copyright, except where explicitly noted. Please contact the author directly with licensing requests."],"dc:subject":["Inorganic chemistry"],"dc:title":["Synthesis of Electron Deficient N-heterocyclic-carbenes and Activity of Imidazol-2-imine Thioureate Ligand on Group 10 Transition Metals"],"dc:type":["Electronic Thesis or Dissertation"]},"updated_at":"2026-07-24T06:33:34Z"}