Date of Award


Degree Name

Master of Arts



First Advisor

Dr. Don C. Iffland

Second Advisor

Dr. Robert Harmon

Third Advisor

Dr. George Lowry

Access Setting

Masters Thesis-Open Access


The kinetics of conformational interchange of 6,6-dicarbethoxydi-benzo- a,c - 1,3 -cyloheptadiene and its 5,5-dideuterated analog were studied using variable temperature NMR techniques. The free energy of activation for conformational interchange of the parent compound was found to be 9.02 kcal mol-1 and that of the 5,5-dideuterated analog to be 9.42 kcal mol-1. Values of the entropy of activation were found to be -19.91 e. u. and -18.12 e. u. respectively. The spectra were recorded on a Nicolet NMC-360 wide bore spectrometer and the data collected treated as an AB spin system.

The 4,8-dideutero, 4,5,5,8-tetradeutero and 5,5,7,7-tetradeutero analogs of the parent compound were also synthesized. Involved in the synthetic procedures is a method for a greatly improved yield in the synthesis of diphenide over what has been previously reported in the literature.

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Chemistry Commons