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March, David Michael (1961) The kinetics of cyclisation of some 2,2'-diphenic acids in sulphuric acid. Doctoral thesis, Sir John Cass College.
The kinetics of cyclisation of 2,2'-diphenic acid have been studied in aqueous sulphuric acid and in sulphuric/acetic acid mixtures over the ranges 77-l00% w/w and 60-l00% w/w H2SO4 respectively.
In an attempt to elucidate the mechanism of the reaction the investigation was extended to certain 5,5'- disubstituted derivatives containing substituents of well-defined electronic character, and also to o-phenyl benzoic acid. These acids were studied in the aqueous medium alone.
In every case a correlation has been found between the specific rate and the acidity of the solvent as given by the Hammett acidity function.
The energy parameters of the reaction have been shown to vary in a marked manner with solvent composition; all the diphenic acids exhibiting the same type of variation; the probable reasons for this have been discussed.
A mechanism has been proposed for the reaction and has been shown to offer a reasonable interpretation of the experimental findings.
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