R. M. Singh, L. Main
1983
Citations
0
Influential Citations
3
Citations
Journal
Australian Journal of Chemistry
Abstract
pH-rate profiles are reported for the hydrolysis of 2-[[{2-hydroxy-1,1-di(hydroxymethyl)ethyl}-imino]methyl]phenol (1) and 1-[[{2-hydroxy-1,1-di(hydroxymethyl)ethyl}imino]methyl]-2-naphthol (2). Rate coefficients for possible contributing reactions are established and compared. Measurement of the rate of hydrolysis in deuterium oxide of (1) in the neutral plateau region of the pH-rate profile shows that the imine (1) is about 1.6 times more reactive in H2O than in D2O, and possible contributing factors to this solvent isotope effect are considered. Also reported are rate data for formation of (1) from 2-amino-2-hydroxymethylpropane-1,3-diol and 2-hydroxybenzaldehyde which show the latter to be almost as reactive in the anionic as in the neutral form; this suggests a base catalysis role by the phenolate oxygen in imine formation.