Date of Award
Bachelor of Science
This thesis was primarily concerned with the correlation of the kinetics and equilibrium of the cinnamaldehyde-bisulfite reaction with the effect of ortho, meta, and para substituents. The cinnamaldehyde-bisulfite reaction is seen below: where X=p-NMe2, p-MeO, p-Me, H, p-Cl, p-Br, p-NO2, m-Br, o-NO2, and o-MeO. The cinnamaldehydes were synthesized via a crossed aldol condensation reaction between acetaldehyde and the corresponding substituted benzaldehyde. The equilibrium constant and second order rate constant for the cinnamaldehyde-bisulfite reaction were determined through UV-visible spectroscopy. The equilibrium and kinetics data was then correlated by Hammet’s equation (log K/KH=pσ°) for the meta and para derivatives. In order to correlate the ortho derivatives, new σ values were derived using a least squares manipulation of NMR 13C chemical shifts.
Hoff, Susanne M., "Linear free energy correlations of the effect of substituents on the cinnamaldehyde-bisulfite reaction" (1990). Honors Theses. 2029.