Date of Award


Publication Type

Master Thesis

Degree Name



Chemistry and Biochemistry

First Advisor

Loeb, Stephen J.,


Chemistry, Inorganic.



Creative Commons License

Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.


This thesis describes the study of two different pairs of heteroditopic macrocyclic ligands. The main emphasis is placed on the synthesis and characterization of the receptor:substrate complexes. In Chapter 2, the synthesis and chemistry of SOX-5 and SOX-6 are explored. The ligands contain separate thiacrown and crown ether moieties linked by an aromatic spacing unit. The two different coordination sites provide locations for the binding of a soft transition metal (Cu(I)), as well as a hard alkali metal ion (Na$\sp{+}$ or K$\sp{+}$) within the same molecule. The haptoselectivity of the ligands was studied by $\sp1$H NMR and X-ray crystallography, with the attainment of the structures of SOX-5, (CuI(SOX-5)) and (CuI(SOX-6)). The main goal was the cooperative coordination of the sodium salts of AMP, ADP and ATP and the appearance of the $\sp1$H NMR spectra is consistent with coordination of NaAMP and NaADP, but not $\rm Na\sb2ATP$. In Chapter 3, a pair of novel receptors are studied. The metallated macrocyclic hosts, $\rm \lbrack Pd(TOMB$-$\rm P4)(CH\sb3CN)\rbrack\sp{+}$ and $\rm \lbrack Pd(TOMB$-$\rm M4)(CH\sb3CN)\rbrack\sp{+}$, employ simultaneous first- and second-sphere coordination to bind aromatic substrates. This is accomplished by $\sigma$-donation to a palladium centre in conjunction with hydrogen bonding and aromatic stacking interactions. The substrates utilized were p-aminopyridine, m-aminopyridine and the nucleobases, adenine, guanine, cytosine and their derivatives, 9-ethyladenine, 9-ethylguanine, l-methylcytosine. (Abstract shortened by UMI.)Dept. of Chemistry and Biochemistry. Paper copy at Leddy Library: Theses & Major Papers - Basement, West Bldg. / Call Number: Thesis1996 .M86. Source: Masters Abstracts International, Volume: 37-01, page: 0267. Adviser: Stephen J. Loeb. Thesis (M.Sc.)--University of Windsor (Canada), 1996.