Nic, Miloslav; (1995) Some studies of through space functional group-arene interactions. Doctoral thesis (Ph.D), UCL (University College London).

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Abstract

This thesis is divided into three chapters. The first chapter is a review, which brings together the available information about the through space aromatic ring interactions from experimental, biological, and theoretical chemistry. The second chapter describes the syntheses of series of novel 9,10[1',4']-benzenoanthracenes and 9,10-propanoanthracenes. Different spectroscopic techniques are used to characterise the behaviour of the title compounds both in solution and in the solid phase. The rigid skeleton of the 9,10[1',4']-benzenoanthracenes allows the position of substituents to be determined unequivocally However, 9,10-propanoanthracenes have a flexible bridge which can flip over the aromatic moiety and thus interactions between the aromatic rings and different functional groups can be compared. A preliminary studies of the influence of solvation on the conformational eqilibria were also performed. A variety of spectroscopic techniques are used to characterize the interactions. These results have given some insight into hydrogen bonding to an aromatic system. The role of a through space interaction on 1H and 13C NMR spectra was also investigated. Chapter three provides a formal description of experimental results and procedures.

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