Back, Thomas GeorgeTuck, Tyler A.2019-08-272019-08-272019-08-23Tuck, T. A. (2019). Antioxidant Activity and Proton Coupled Electron Transfer Processes in Conformationally Restricted Naphthalene peri-Dichalcogenides (Master's thesis, University of Calgary, Calgary, Canada). Retrieved from https://prism.ucalgary.ca.http://hdl.handle.net/1880/110823Conformationally restricted naphthalene peri-dichalcogenides are powerful mimetics of the selenoenzyme glutathione peroxidase (GPx), and form charge transfer complexes with the electron acceptor tetracyanoquinodimethane (TCNQ). More recently, the Back group has discovered that these molecules display unusual NMR behaviour. This thesis describes a thorough investigation into this NMR behaviour, which is attributed to a proton-coupled electron transfer process (PCET) between the dichalcogenide and its own conjugate acid to form a radical and a radical cation. Evidence supporting this conclusion comes from NMR experiments, EPR spectroscopy, reversibility with sodium dithionite, as well as computational results. Most conformationally restricted naphthalene peri-diselenides synthesized thus far have poor water solublity, a major limitation to serve as GPx mimetics. The second part of this thesis will describe attempts to alleviate this issue by describing the synthesis and GPx like activity of more polar conformationally restricted naphthalene peri-diselenides.engUniversity of Calgary graduate students retain copyright ownership and moral rights for their thesis. You may use this material in any way that is permitted by the Copyright Act or through licensing that has been assigned to the document. For uses that are not allowable under copyright legislation or licensing, you are required to seek permission.AntioxidantSeleniumChemistryChemistry--OrganicEngineering--Chemicalmaster thesis10.11575/PRISM/36905