Mass spectrometry, mechanisms, and molecular models - combining research in mass spectrometric reaction monitoring and chemical education

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dc.contributor.authorDean, Natalie L.
dc.contributor.supervisorMcIndoe, J. Scott
dc.date.accessioned2018-05-18T17:24:23Z
dc.date.available2018-05-18T17:24:23Z
dc.date.copyright2018en_US
dc.date.issued2018-05-18
dc.degree.departmentDepartment of Chemistry
dc.degree.levelMaster of Science M.Sc.en_US
dc.description.abstractThis thesis combines work in the areas of mass spectrometric reaction monitoring and chemical education. In the first part of this thesis, real-time mechanistic analysis using electrospray ionization mass spectrometry is reported. In Chapter 1, an introduction to the mass spectrometric instrumentation and methodologies used in this research is provided. In Chapter 2, the real-time mechanistic analysis of the Hiyama cross-coupling reaction using electrospray ionization mass spectrometry is reported, in particular, the fluoride-mediated rearrangement of phenylfluorosilanes that was found to occur even before catalyst addition. Combining Ph3SiF with a fluoride ion source under typical Hiyama cross-coupling conditions causes rapid formation of the expected [Ph3SiF2]–; however, ESI-MS analysis reveals that phenyl-fluoride exchange occurs concomitantly, also producing substantial quantities of [PhnSiF5–n]– (n = 0-2). The exchange process is verified using 19F NMR spectroscopy. This observation may have implications for Hiyama reaction protocols, which use transmetallation from triaryldifluorosilicates as a key step in cross-coupling. Optimization of the methodology used for real-time analysis by ESI-MS to reduce observed contamination from leaching of rubber septa additives is also discussed. In the second part of this thesis, the development and application of two different approaches for generating molecular models for the teaching molecular geometry and VSEPR theory in first year chemistry is reported. Chapter 4 details a method for the application of handheld 3D printing pens for producing models from ABS plastic. In Chapter 5, the development of laser-cut acrylic model kits is detailed, as well as the design and results of a quantitative study aimed at assessing their effectiveness for improving representational competence and comprehension of molecular geometry.en_US
dc.description.scholarlevelGraduateen_US
dc.identifier.bibliographicCitation“Applying Handheld 3D Printing Technology to the Teaching of VSEPR Theory” N. L. Dean, C. Ewan, and J. S. McIndoe. J. Chem. Ed., 2016, 93, 1660-1662.en_US
dc.identifier.bibliographicCitation
dc.identifier.urihttp://hdl.handle.net/1828/9383
dc.languageEnglisheng
dc.language.isoenen_US
dc.rightsAvailable to the World Wide Weben_US
dc.subjectMass Spectrometryen_US
dc.subjectChemical Educationen_US
dc.subjectVSEPRen_US
dc.subjectHiyama Cross-Couplingen_US
dc.subjectFluorophenylsilaneen_US
dc.subjectMolecular Geometryen_US
dc.titleMass spectrometry, mechanisms, and molecular models - combining research in mass spectrometric reaction monitoring and chemical educationen_US
dc.typeThesisen_US

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