Date of Award

Winter 1987

Project Type


Program or Major


Degree Name

Doctor of Philosophy

First Advisor

G R Weisman


A series of dipodands (2, 4 and 9) as well as tripodands (13, 18, 20, 26 and 31) have been synthesized and characterized. The general synthetic methodology followed involves alkylation of the cyclohexane-based alcohols with the "arm" tosylates.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI).

The conformational aspects governing the complexation of these podands with alkali metal ions were studied by $\sp1$H NMR, $\sp{13}$C NMR and $\sp{13}$C dynamic NMR supported by complementary molecular mechanics studies. The relative complexing abilities of 2 and comformationally biased 9 have been measured by $\sp{13}$C NMR competition experiments.

Lipophilic podand 18 and model 13 were studied for the possibility of micellar behavior of these molecules. The relative complexing abilities of podands 37, 13, 18 and 2 were compared by competition experiments.

"Extra long arm" podands 26 and 31 were found to be capable of complexing two Na$\sp+$ ions. The Na$\sp+$--Na$\sp+$ distance was estimated by CPK models to be approximately 3.2 A$\sp{\rm o}$.

A concentration dependence study of 1:1 mixture of complex to free ligand was done in CDCl$\sb3$ by $\sp{13}$C dynamic NMR. (Abstract shortened with permission of author.).