The work presented in this thesis falls into four parts. In Chapter 1 results are presented for the detritiation of a number of substituted 2-([3H]-acetyl) thiophenes. These show that when a carboxyl group is present adjacent to the ionising acetyl group intramolecular catalysis makes an important contribution to the overall rate although the effective molarity is no higher than the other base catalysed proton transfers previously reported in the literature. Proton transfer reactions involving the ionisation of carbon acids have usually been studied in aqueous conditions. In Chapter 2 the development of a detritiation procedure for non-aqueous conditions is reported and the method used to establish an order of basicity for a large number of amines in dimethyl sulphoxide. The following chapter extends the investigation carried out in Chapter 2 to a range of other solvents. The results show a marked similarity in relative rates for detritiation of acetophenone as catalysed by a number of amines in these solvents. The ability of enzymes to catalyse many reactions under very mild conditions has prompted chemists to investigate whether they can design molecules that are just as effective. In the last chapter a preliminary investigation has been made to see how amines, when they are part of a macromolecular framework, perform as catalysts.