Electrochemical Investigation of N-(Arylthio)phthalimides and Arylmethylphthalimidosulfonium Hexachloroantimonate Salts

dc.contributor.advisorAbdelaziz, Houmam
dc.contributor.authorSaley, Michael
dc.date.accessioned2019-09-11T20:04:13Z
dc.date.available2019-09-11T20:04:13Z
dc.date.copyright2019-09
dc.date.created2019-08-28
dc.date.issued2019-09-11
dc.degree.departmentDepartment of Chemistryen_US
dc.degree.grantorUniversity of Guelphen_US
dc.degree.nameMaster of Scienceen_US
dc.degree.programmeChemistryen_US
dc.description.abstractA series of N-(arylthio)phthalimides was synthesized. The electrochemical reduction of N-(arylthio)phthalimides follows a stepwise mechanism, generating a radical anion intermediate. Computational analysis suggests the nitro derivative follows a different radical anion dissociation mechanism, meaning the substituent effect should be opposite to that observed. Rigorous application of dissociative electron transfer theory and gas phase calculations allow the rationalization of this phenomena. The N-(arylthio)phthalimides were also investigated as precursors for self assembled monolayer formation (SAM) on Au, where the nitro derivative showed excellent activity as a precursor. A series of arylmethylphthalimidosulfonium hexachloroantimonate salts was synthesized. The electrochemical reduction of the series follows a concerted mechanism. The investigation revealed a change in regioselectivity as a function of the aromatic substituent. For all species except the nitro derivative the S+―N cleavage was observed. For the nitro derivative the S+―CH3 cleavage was observed. The regioselectivity was rationalized on the basis of the gas phase calculations.en_US
dc.description.sponsorshipNatural Sciences and Engineering Research Council of Canada
dc.identifier.urihttp://hdl.handle.net/10214/17444
dc.language.isoenen_US
dc.publisherUniversity of Guelphen_US
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subjectElectrochemistryen_US
dc.subjectElectron Transferen_US
dc.subjectCyclic Voltammetryen_US
dc.subjectElectrolysisen_US
dc.subjectN-(arylthio)phthalimideen_US
dc.subjectarylmethylphthalimidosulfoniumen_US
dc.subjectScanning Tunneling Microscopyen_US
dc.subjectSelf Assembled Monolayeren_US
dc.titleElectrochemical Investigation of N-(Arylthio)phthalimides and Arylmethylphthalimidosulfonium Hexachloroantimonate Saltsen_US
dc.typeThesisen_US

Files

Original bundle
Now showing 1 - 1 of 1
Loading...
Thumbnail Image
Name:
Saley_Michael_201908_MSc.pdf
Size:
2.61 MB
Format:
Adobe Portable Document Format
Description:
Full thesis document