Linear free energy correlations of the effect of substituents on the cinnamaldehyde-bisulfite reaction

Author

Susanne M. Hoff, Union College - Schenectady, NY

Date of Award

6-1990

Document Type

Open Access

Degree Name

Bachelor of Science

Department

Chemistry

Language

English

Abstract

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.

Recommended Citation

Hoff, Susanne M., "Linear free energy correlations of the effect of substituents on the cinnamaldehyde-bisulfite reaction" (1990). Honors Theses. 2029.
https://digitalworks.union.edu/theses/2029