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Title: Optical stability and spectroscopic studies of 1,1-binaphthyl and related compounds
Author: Mazengo, Richard
Awarding Body: University of London
Current Institution: Royal Holloway, University of London
Date of Award: 1968
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Previous work on tlie optical stabilities of substituted 1,1'-binaphthyls has shown that the energy of activation for the racemisation of optically active 1,1'-binaphtliyls with Planar substituents in the 8,8- positions is almost identical with that of unsubstituted 1,1'-binaphthyl. 8'-Methyl-1,1'-binaphthyl-8-carboxylic acid has been prepared, resolved and its Arrhenius parameters and transition state theory functions for racemisation determined. The values of , and A S are remarkably close to those of 8-methyl-1,1'-binaphthyl and it is concluded that here again the -COOH group offers a negligible steric barrier to the transition state for racemisation. Optically active 2,2'-dimethyl-1,1'-binaphthyl has been synthesised and found to be highly optically stable; this is explained on the basis that its ground state energy is much lower than that of an 8,8'-substituted 1,1'-binaphthyl. Attention was then turned to an investigation of the ground states of certain of the substituted 1,1'-binaphthyls using , mass spectra, O.R.D. and C.D. Ultraviolet spectra indicate that the 8,8'-substituted 1,1'-binaphthyls are overall more "planar" than 2,2'-substituted 1,1'-binaphthyls. Nuclear magnetic resonance spectra indicate that the substituents in the 2,2'- positions are further away.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Organic Chemistry