The effects of solvent and substituents upon the ionization of phenols
| dc.contributor.author | Leary, G. J. | en |
| dc.date.accessioned | 2014-07-20T22:10:46Z | |
| dc.date.available | 2014-07-20T22:10:46Z | |
| dc.date.issued | 1964 | en |
| dc.description.abstract | The “dissociation constants” of a series of 4-substituted-phenols, 4-substituted-2,6-dichlorophenols, and 4-substituted-2,6-dimethylphenols have been measured potentiometrically in a variety of solvents. Excellent linear Hammett plots are obtained for each series in all solvents. The effects of changing solvent upon the Hammett ρ values for each of these three series are deduced from these measurements. As the “solvating power” of the solvent is reduced ρ for each series increases because of the increased demand placed on the 4-substituent for dispersal of the anionic charge. Within each solvent ρ is greater for the 2,6-disubstituted-phenols than for the unhindered phenols. The 2,6-substituents hinder solvation and tis increases the demand for anionic charge dispersal by the 4-substituent. 2,6-Dichloro- or 2,6-Dimethyl-substitution is found to hinder solvation of the phenoxide ion even in water. The solvent-dependence of the Hammett σρ values is discussed and some attempt is made to interpret the shape of the potentiometric titration curves in different solvents. | en |
| dc.identifier.uri | http://hdl.handle.net/10092/9390 | |
| dc.identifier.uri | http://dx.doi.org/10.26021/6823 | |
| dc.language.iso | en | |
| dc.publisher | University of Canterbury. Chemistry | en |
| dc.relation.isreferencedby | NZCU | en |
| dc.rights | Copyright G. J. Leary | en |
| dc.rights.uri | https://canterbury.libguides.com/rights/theses | en |
| dc.title | The effects of solvent and substituents upon the ionization of phenols | en |
| dc.type | Theses / Dissertations | |
| thesis.degree.discipline | Chemistry | |
| thesis.degree.grantor | University of Canterbury | en |
| thesis.degree.level | Doctoral | en |
| thesis.degree.name | Doctor of Philosophy | en |
| uc.bibnumber | 347506 | |
| uc.college | Faculty of Science | en |
Files
Original bundle
1 - 1 of 1