Date of Award


Document Type


Degree Name

Doctor of Philosophy (PhD)


A series of five macrocyclic 1,3-diketones has been produced. and characterized by infrared, nuclear magnetic resonance, mass. spectroscopy and elemental analysis. The series consists of. compounds of the type where n = 4,6,7,8 and 10. A survey was conducted to determine the ability of these ligands to form complexes with twelve different metals. The metals used in the study were Be(II), Mg(II), Al(III), Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Pd(II) and Cd(II). Considerable selectivity was observed in the chelation reactions of these ligands, where only the ligands having 10, 11 and 13 carbon atoms formed chelates. Selectivity increased with decreasing ring size with the C(,10) ligand forming chelates only with Fe(III) and Cu(II). The chelates formed were tested for extraction in five different solvents and for volatility in the Berg fractional sublimator. The copper chelates were further characterized by infrared mass spectroscopy as well as by elemental and metal analysis. An attempt was made to prepare a series of macrocyclic bis-. 1,3-diketones of the type where n = 4,6,7,8 and 10 but only the. n = 7 and 8 tetraketones were prepared and these in low yields. These two tetraketones were characterized by infrared and mass spectroscopy. A comparison was made of the volatility of the copper chelates of the 22 carbon tetraketone and the 11 carbon diketone.