{"id":{"repo_id":"mo-state","oai_identifier":"oai:bearworks.missouristate.edu:theses-1364"},"canonical_url":"https://search.dev.ndltd.org/etd/mo-state/oai:bearworks.missouristate.edu:theses-1364","repository":{"repo_id":"mo-state","name":"Missouri State University","base_url":"https://bearworks.missouristate.edu/do/oai/"},"display":{"title":"Reactivity of the Vinylogous Epoxyketone Moiety","abstract":"The lipid peroxidation process produces lipid hydroperoxides which decompose to a variety of secondary lipid peroxidation products such as epoxides, aldehydes, and ketones. A vinylogous epoxyketone, 5,6-epoxy-3-nonen-2-one was chosen as a model of one lipid oxidation product. The synthesis and characterization of the model are presented. The reactivity of the model was predicted from molecular orbital calculations and the hard and soft acid base (HSAB) theory. These results are compared to experimental results obtained from adding various nucleophiles. A hard nucleophile, phenyl lithium, was shown to add according to predications based on the HSAB theory. The reactivity of a soft nucleophile, the enolate of diethyl malonate, was not explained by the HSAB theory but by other factors such as ring strain and steric hindrance of the epoxide ring.","abstract_html":"The lipid peroxidation process produces lipid hydroperoxides which decompose to a variety of secondary lipid peroxidation products such as epoxides, aldehydes, and ketones. A vinylogous epoxyketone, 5,6-epoxy-3-nonen-2-one was chosen as a model of one lipid oxidation product. The synthesis and characterization of the model are presented. The reactivity of the model was predicted from molecular orbital calculations and the hard and soft acid base (HSAB) theory. These results are compared to experimental results obtained from adding various nucleophiles. A hard nucleophile, phenyl lithium, was shown to add according to predications based on the HSAB theory. The reactivity of a soft nucleophile, the enolate of diethyl malonate, was not explained by the HSAB theory but by other factors such as ring strain and steric hindrance of the epoxide ring.","abstract_has_math":false,"creators":["Martin, Robert Scott"],"institution":null,"degree_name":"Master of Science in Chemistry","degree_level":"Masters","degree_discipline":"Chemistry and Biochemistry","degree_department":null,"school":null,"contributors":["Tamera Jahnke"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":1996,"date_issued":"1996-01-01T08:00:00Z","date_published":"1996-01-01T08:00:00Z","updated_at":"2026-07-24T03:15:29Z","subjects":["Chemistry"],"languages":[],"rights":["© Robert Scott Martin"],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://bearworks.missouristate.edu/theses/363","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Tamera Jahnke"]},{"key":"dc:creator","label":"Author","values":["Martin, Robert Scott"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry and Biochemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Masters"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science in Chemistry"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:rights","label":"Dc Rights","values":["© Robert Scott Martin"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://bearworks.missouristate.edu/theses/363"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The lipid peroxidation process produces lipid hydroperoxides which decompose to a variety of secondary lipid peroxidation products such as epoxides, aldehydes, and ketones. A vinylogous epoxyketone, 5,6-epoxy-3-nonen-2-one was chosen as a model of one lipid oxidation product. The synthesis and characterization of the model are presented. The reactivity of the model was predicted from molecular orbital calculations and the hard and soft acid base (HSAB) theory. These results are compared to experimental results obtained from adding various nucleophiles. A hard nucleophile, phenyl lithium, was shown to add according to predications based on the HSAB theory. The reactivity of a soft nucleophile, the enolate of diethyl malonate, was not explained by the HSAB theory but by other factors such as ring strain and steric hindrance of the epoxide ring."]},{"key":"dc:title","label":"Title","values":["Reactivity of the Vinylogous Epoxyketone Moiety"]}]}],"canonical_facts":{"dc:contributor":["Tamera Jahnke"],"dc:creator":["Martin, Robert Scott"],"dc:description.abstract":["The lipid peroxidation process produces lipid hydroperoxides which decompose to a variety of secondary lipid peroxidation products such as epoxides, aldehydes, and ketones. A vinylogous epoxyketone, 5,6-epoxy-3-nonen-2-one was chosen as a model of one lipid oxidation product. The synthesis and characterization of the model are presented. The reactivity of the model was predicted from molecular orbital calculations and the hard and soft acid base (HSAB) theory. These results are compared to experimental results obtained from adding various nucleophiles. A hard nucleophile, phenyl lithium, was shown to add according to predications based on the HSAB theory. The reactivity of a soft nucleophile, the enolate of diethyl malonate, was not explained by the HSAB theory but by other factors such as ring strain and steric hindrance of the epoxide ring."],"dc:identifier":["https://bearworks.missouristate.edu/theses/363"],"dc:rights":["© Robert Scott Martin"],"dc:subject":["Chemistry"],"dc:title":["Reactivity of the Vinylogous Epoxyketone Moiety"],"thesis:degree_discipline":["Chemistry and Biochemistry"],"thesis:degree_level":["Masters"],"thesis:degree_name":["Master of Science in Chemistry"]},"updated_at":"2026-07-24T03:15:29Z"}