Structure and Solution Equilibrium of N-Salicylidene-amino-sugars and Amino-alcohols.

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Abstract
The structures and solution equilibria of 20 members of N-salicylidene-amino-sugars and -amino-alcohols were examined mainly in methanol, water and solid state. As the modeled compounds were examined simultaneously, 3 members of N-salicylidene-alkyl-amines and 8 members belonged to the o-methoxybenzylidene, 3-methoxysalicylidene, 3,5-dibromosali-cylidene and 2-hydroxynaphthylidene derivatives. Comparative studies on the electronic, IF, NMR [nuclear magnetic resonance] spectra and equilibrium position, indicated that the solution equilibrium consisted of the phenolimine and the ketoamine species, the latter being stabilized by the intra- and intermolecular hydrogen bonding involving the alcoholic hydroxyl groups and protic solvents. The acid-base equilibria of the 2 tautomers in methanol and the ketoamine-ion-pair equilibrium in water were discussed.

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