Determination of sugar hydrazide and hydrazone structures in solution

Condensation products of isonicotino- and benzo-hydrazide, and p-bromophenylhydrazine with d-glucose, d-mannose, d-arabinose, and d-ribose, respectively, and of isonicotinohydrazide with sodium d-glucuronate, d-glucofuranurono-6,3-lactone, and d-glyceraldehyde were prepared. The structure of the compounds in solution was examined by ¹H- and ¹³C-n.m.r. spectroscopy and optical rotation, and in solid state by i.r. spectroscopy. The study of the anomerization and ring-chain interconversion on solutions in various solvents showed that both anomerization and interconversion depend upon the sugar configuration, basicity of the hydrazine group, and proton-acceptor ability of the solvent.