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Title: | Kinetic Study of Thermal Decarboxylation of Substituted Sodium Phenylpropiolates |
Other Titles: | Decarboxylation of Substituted Sodium Phenylpropiolates |
Authors: | Wong, Edward |
Advisor: | Bourne, A. N. |
Department: | Chemistry |
Keywords: | kinetic;thermal decarboxylation;decaroboxylation;sodium phenylpropiolates |
Publication Date: | Sep-1961 |
Abstract: | The kinetics of the thermal decarboxylation of a series of substituted sodium phenylpropiolates were studied in detail. The reaction proceeded without formation of significant amounts of side products: its rate was independent of hydrogen ion concentration. The relative rates of decarboxylation are in the order: p-NO2 > m-NO2> m-CF3 > m-Cl > p-Cl > H > m-CH3, and the entropies of activation are large and positive. The results were discussed in terms of the unimolecular (SE1) mechanism. A quantitative study of effects of substituents on the decarboxylation rates was made by the application of the Hammett free energy relationship. The e value of the Hammett plot was 0.886 +/- 0.013. Deviation of para substituted compounds from the Hammett relationship were discussed in terms of para interaction or conjugation effects in the initial or the transition states. |
URI: | http://hdl.handle.net/11375/23592 |
Appears in Collections: | Digitized Open Access Dissertations and Theses |
Files in This Item:
File | Description | Size | Format | |
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wong_edward_w_c_1961Sep_masters.pdf | 32.97 MB | Adobe PDF | View/Open |
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