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Kinetic and Mechanistic Studies of Decarboxylation

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dc.contributor.author Tate, Kevin Russel
dc.date.accessioned 2008-09-05T02:59:56Z
dc.date.accessioned 2022-10-12T19:08:06Z
dc.date.available 2008-09-05T02:59:56Z
dc.date.available 2022-10-12T19:08:06Z
dc.date.copyright 1968
dc.date.issued 1968
dc.identifier.uri https://ir.wgtn.ac.nz/handle/123456789/21813
dc.description.abstract A kinetic investigation of 2,4- and 2,6-dimethoxybenzoic acid has been undertaken, in an attempt to resolve questions of mechanism which a study of 2,4,6-trimethoxybenzoic acid 9 had been unable to do. The presence of the strongly releasing methoxyl groups in positions ortho and para to the carboxyl group, should facilitate the electrophilic process, as in the case of the trisubstituted acid. Oxocarbonium ion (i.e. ArCO+) formation was not expected to be appreciable for 2,4-dimethoxybenzoic acid, where steric compression of the carboxyl group is considerably reduced by the presence of only one ortho methoxyl group. Although the subject of reaction kinetics in concentrated mineral acids has been generally confused, some order has recently been restored by Bunnett et al,16 in an attempt to classify reaction mechanisms in these media. While their treatment still requires an understanding of why some compounds protonate in accordance with the Hammett acidity function, Ho, and others do not, it was hoped that an application to the kinetic data for the decarboxylation reactions might provide an insight into mechanism. In addition, kinetic carbon-13 and solvent deuterium isotope effects, have been employed in an attempt to identify the rate limiting process (or processes). A mechanism has been proposed for the decarboxylation of the methoxybenzoic acids. A similar kinetic investigation of the decarboxylation of the 2,4-, 2,6- and 2,4,6-hydroxybenzoic acids has been carried out, to compare and contrast differences in mechanism with the corresponding methoxybenzoic acids. en_NZ
dc.format pdf en_NZ
dc.language en_NZ
dc.language.iso en_NZ
dc.publisher Te Herenga Waka—Victoria University of Wellington en_NZ
dc.title Kinetic and Mechanistic Studies of Decarboxylation en_NZ
dc.type Text en_NZ
vuwschema.type.vuw Awarded Doctoral Thesis en_NZ
thesis.degree.grantor Te Herenga Waka—Victoria University of Wellington en_NZ
thesis.degree.level Doctoral en_NZ
thesis.degree.name Doctor of Philosophy en_NZ

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