Date of Award

Fall 1989

Project Type


Program or Major


Degree Name

Doctor of Philosophy

First Advisor

Paul R Jones


The synthesis, characterization and ring-chain tautomerism studies of substituted 2-(2-hydroxyethoxy)-benzaldehydes and 2-(5-hydroxy-3-oxa-pentyloxy)-benzaldehydes are described. The benzaldehydes, substituted in the 3-, 5- or 3,5-positions with either nitro, bromo, chloro, iodo, phenyl or methyl groups, were studied by proton and carbon-13 Nuclear Magnetic Resonance spectroscopy as a means of determining their potential to exist as ring-chain tautomeric mixtures. The 2-(5-hydroxy-3-oxa-pentyloxy)-benzaldehydes and 5-substituted 2-(2-hydroxyethoxy)-benzaldehydes exist solely as the chain tautomers in solution, while 3- and 3,5-substituted 2-(2-hydroxyethoxy)-benzaldehydes are mixtures of ring and chain tautomers in solution. A correlation of K with substituents indicates that the size of the aromatic substituent in the 3-position is the key factor in affecting the equilibrium.