Structure and reactivity of selected organic inclusion compounds

Doctoral Thesis

2002

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University of Cape Town

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The inclusion behaviour of the two host compounds 1,1 ,6,6-tetraphenylhexa-2,4- diyne-l,6-diol and cyclotriveratrylene (2,3,7,8,12,13-hexamethoxy-5,lO-dihydro- 15H-tribenzo[ a,d,g]cyclononene) was studied. Small organic guests were complexed with these hosts and their crystal structures determined. The stability and reactivity of these inclusion compounds were investigated. Kinetics of desolvation were determined for some of the inclusion compounds using both isothermal and non-isothermal methods. Rate laws were proposed and activation energies established. The selectivity of the host 1,1 ,6,6-tetraphenylhexa-2,4-diyne- 1,6-diol for certain guests was determined by competition experiments. Lattice energies were calculated in some cases. Solid state reactions were performed with the host 1,1 ,6,6-tetraphenylhexa-2,4-diyne-1 ,6-diol and selected solid guests. The resultant complexes were analysed using X-ray powder diffraction. Guest exchange reactions were also performed and the reactions were monitored either by differential scanning calorimetry or thermogravimetry. The structures of the inclusion compounds were reconciled with their physico-chemical properties.
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