Publication Date


Document Type


First Advisor

Rogers, Robin D.

Degree Name

M.S. (Master of Science)

Legacy Department

Department of Chemistry


Crown ethers; Organonitrogen compounds; Lanthanum compounds; Organosodium compounds


The study of the chemistry of macrocycles and their complexes is a field encompassing goals as diverse as extraction, catalysis, and modeling of biological systems. The development of new macrocycles brings the possibility of achieving these goals that much closer. In this spirit, several new macrocycles and their complexes have been synthesized and characterized using X-ray diffraction, elemental analysis, and spectroscopic techniques. The compounds studied include the nitrated derivatives of benzo-15-crown-5 and dibenzo-18-crown-6, methylene-16-crown-5 and its complexes, and hexadentate Schiff base complexes of the lanthanides. Nitrobenzo-15-crown-5, dinitrobenzo-15-crown-5, dinitrodibenzo-18-crown-6, and methylene-16-crown-5 were investigated as possible synthetic precursors to more complex crowns. The three nitro-crowns and a sodium thiocyanate complex with nitrobenzo-15-crown-5 were structurally investigated. The three nitro-crowns were found to be structurally similar to their parent compounds. The sodium thiocyanate complex was shown to be similar to sodium complexes of benzo-15-crown-5. Methylene-16-crown-5 complexes of sodium iodide and sodium nitrite were prepared and structurally characterized. A complex of dimethylene-26-crown-8 with sodium iodide was structurally characterized in the course of this study as was a complex of cerium chloride heptahydrate with tetraethylene glycol dimethyl ether. Schiff base complexes of the lanthanides were investigated as examples of compounds with interactions between hard metal cations and soft donors. Sulfur was used as the soft donor. The interactions between the lanthanides and imine donors found in Schiff base macrocycles have been shown to be surprisingly stable. This stability was used to increase the overall stability of the complex, to some degree compensating for the instability of the lanthanide sulfur interaction.


Includes bibliographical references (pages [125]-128)


xi, 128 pages




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