A study of some non-covalent functional group-arene interactions
This thesis describes an investigation of the weak non-covalent interactions between the 7r-system of an aromatic ring and various functional groups. The first section comprises a review of the current literature on the through space aromatic ring interactions based on theoretical, biological and experimental chemistry and especially focuses on the -interactions involving a functional group. The second section describes the synthesis of a series of novel 9,10-propanoanthracenes, with a common framework, consisting of a rigid structure containing two independent aromatic systems and a flexible bridge. The central carbon atom of the bridge can be substituted with two different functional groups, which are held in close proximity to the centre of one of the aromatic rings. This gives rise to two possible conformers, whose population relies on the difference in the strength of the interactions between the aromatic ring and each substituent of the bridge, relative to the solvent being employed. The conformational equilibria of each derivative were studied by NMR spectroscopy using variable temperature techniques and solvents. The presumed equilibria under those two variables were compared in order to give some insight into the nature of the n interactions involved. The thesis concludes with a formal account of the experimental procedures used, the compounds prepared and an appendix detailing theoretical data obtained by computational chemistry and crystal structures data.