- Title
- The synthesis and analysis of (2R,3R)-1,1,4,4- tetraphenylbutane-1,2,3,4-tetraol (tetrol) and derivatives, and a study of their host potential
- Creator
- Weitz, Selwyn Herbert
- Subject
- Chemistry, Organic
- Date Issued
- 2015
- Date
- 2015
- Type
- Thesis
- Type
- Masters
- Type
- MSc
- Identifier
- http://hdl.handle.net/10948/3735
- Identifier
- vital:20459
- Description
- This investigation focussed on the inclusion and resolution ability of (2R,3R)-1,1,4,4-tetraphenylbutane-1,2,3,4-tetraol (TETROL), studies on the stoichiometry of its derivatives and the formation of inclusion compounds for single crystal analysis. The guest compounds that featured in the main study were cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone and 4-methylcyclohexanone. It was found that 3- and 4-methylcyclohexanone were trapped in their energetically unfavourable axial conformations in the inclusion crystal. Resolution experiments proved that (2R,3R)-1,1,4,4-tetraphenylbutane-1,2,3,4-tetraol can be used as a resolving agent for 2- and 3-methylcyclohexanone, with ee values of 13% and 22%, respectively (according to the method of Hiemstra), in favour of the R-enantiomer. Single crystal X-ray diffraction (SCXRD) studies, however, showed that 2-methylcyclohexanone was resolved with an ee of 30% in R. An ee of 56% in R was obtained for 3-methylcyclohexanone. Enantiomer enrichment of 2-methylcyclohexanone was achieved in basic medium (ee of 18% according to the method of Hiemstra) and showed that by using the host in either half or double the molar ratio of the guest, a higher ee was obtained than for a 1:1 ratio. The following TETROL derivatives were also synthesized and their stoichiometries with various guest compounds were determined: (2R,3R)-1,1,4,4-tetra(naphthalen-1-yl)butane-1,2,3,4-tetraol; (2R,3R)-1,1,4,4-tetra(naphthalen-2-yl)butane-1,2,3,4-tetraol; (2R,3R)-1,1,4,4-tetra(p-anisyl)butane-1,2,3,4-tetraol; (2R,3R)-1,1,4,4-tetra(p-tolyl)butane-1,2,3,4-tetraol; (2R,3R)-1,1,4,4-tetra(m-tolyl)butane-1,2,3,4-tetraol and; (2R,3R)-1,1,4,4-tetra(o-tolyl)butane-1,2,3,4-tetraol.
- Format
- v, 136 leaves
- Format
- Publisher
- Nelson Mandela Metropolitan University
- Publisher
- Faculty of Science
- Language
- English
- Rights
- Nelson Mandela Metropolitan University
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NMMU School of BioMolecular and Chemical Sciences
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