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Goldup, Alan (1958) The bromination of aromatic polycyclic hydrocarbons and its use in analysis. Doctoral thesis, Sir John Cass College.
This thesis describes an analytical technique for confirming the presence of polycyclic aromatic hydrocarbons by the preparation and identification of their bromine derivatives. These are identified by their characteristic ultra-violet spectra either before or after separation by absorption chromatography.
The direct bromination of polycyclic aromatic hydrocarbons normally occurring in combustion products has been reviewed and the preparation of a number of previously unknown bromine derivatives is described.
A study of the ultra-violet absorption spectra of bromine substituted polycyclic aromatic hydrocarbons has shown that bromination displaces the various bands bathochromically by different amounts and that both the extent of displacement and the change in intensity of a band are dependent upon the position of substitution.
The adsorption chromatography of polycyclic aromatic hydrocarbons and their bromine derivatives on alumina has also also been studied. It has been found that the direct bromination of completely benzenoid polycyclic hydrocarbons produces a reduction in absorbability and that this becomes progressively greater as the extent of substitution increases. This has been attributed to a reduction in hydrogen bonding between the adsorbent and adsorptive resulting from a replacement of active hydrogen atoms by bromine.
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