Date of Award
8-1984
Degree Name
Master of Arts
Department
Chemistry
First Advisor
Dr. Don C. Iffland
Second Advisor
Dr. Robert Harmon
Third Advisor
Dr. George Lowry
Access Setting
Masters Thesis-Open Access
Abstract
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.
Recommended Citation
Jonas, Patrick F., "I. A Temperature Dependent NMR Study of 6,6-Dicarbethoxy-5,5-Dideuteodi-Benzo--[a,c]-[l, 3]-Cycloheptadiene II. The Synthesis of Four Deuterated Analogs of 6, 6-Dicarbethoxydibenzo-[a,c]-[1,3]-Cycloheptadiene" (1984). Masters Theses. 1536.
https://scholarworks.wmich.edu/masters_theses/1536