Study of 1-metalated-2-(trimethylsilyl)vinyl cations: An examination of the β-effect for silyl, germyl and stannyl groups

Dallaire, Carol

Please use this identifier to cite or link to this item: http://hdl.handle.net/11375/8398

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DC Field	Value	Language
dc.contributor.advisor	Brook, Michael A.	en_US
dc.contributor.author	Dallaire, Carol	en_US
dc.date.accessioned	2014-06-18T16:42:48Z	-
dc.date.available	2014-06-18T16:42:48Z	-
dc.date.created	2010-12-02	en_US
dc.date.issued	1991-09	en_US
dc.identifier.other	opendissertations/3605	en_US
dc.identifier.other	4622	en_US
dc.identifier.other	1669047	en_US
dc.identifier.uri	http://hdl.handle.net/11375/8398	-
dc.description.abstract	<p>The ability of silicon, germanium and tin elements (group 14) to stabilize a vinyl cation intermediate was investigated upon proton addition to metalated (trimethylsilyl)acetylene compounds to lead, after demetalation, to monometalated acetylenes. The reactions were followed by ¹H NMR spectroscopy. A bimolecular addition mechanism is obtained and nucleophilic participation in the reaction is observed. The reaction rates showed that vinyl cations are stabilized by hyperconjugation of the carbon-metal bond (β-effect) in the order of magnitude Sn (10⁸) > Ge (500) > Si (1). The magnitude of the β-effect on vinyl cation is altered to a degree by the groups born by the metal. The vinyl cations are stabilized, in a lower extent, by inductive effects of the metalated group to the electron-deficient carbon (α-effect).</p>	en_US
dc.subject	Chemistry	en_US
dc.subject	Chemistry	en_US
dc.title	Study of 1-metalated-2-(trimethylsilyl)vinyl cations: An examination of the β-effect for silyl, germyl and stannyl groups	en_US
dc.type	thesis	en_US
dc.contributor.department	Chemistry	en_US
dc.description.degree	Doctor of Philosophy (PhD)	en_US
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