Date of Award
Master of Science in Chemistry - (M.S.)
Chemical Engineering, Chemistry and Environmental Science
Carol A. Venanzi
In order to measure nitrogen and oxygen ionization energies of planar and nonplanar lactams, four compounds were synthesized successfully. The comparison of these ionization energies provides a qualitative insight into how the charge distribution of strained lactams varies with molecular geometry. Of special interest was the different ability of amides to exhibit resonance, monitored most sensitively by the core electron energy of nitrogen in the compounds. The nitrogen core (1s) ionization energies for the two nonplanar amides, 1,3-di-tert-butyl aziridinone (405.00 ev) and 1-azabicyclo[3.3.1]nonan-2-one (405.47) each having pyramidal nitrogens, indicated a nitrogen more negative than that in the comparable planar amide. This result is in accord with the classical view of amide bonding. An attempt to synthesize a bridgehead lactam 8,8,9,9-tetramethy1-1-azabicyclo[3.3.1]nonan-2-one was not successful and a postulated structure for the unanticipated product was proposed.
Tsai, Jung-Chou, "Synthesis of strained lactams and study of their energetics and bonding" (1990). Theses. 1944.