Add time:09/01/2019         Source:sciencedirect.com

The structures of xylo-4,5,6,-trihydroxy-2-oxo-1,3-bis(phenylhydrazono)cyclohexane (1), 2-oxo-1,3-bis(phenylhydrazono)cyclohexane (2), 2-oxo-1,3-bis(phenylhydrazono)cyclopentane (3),3-oxo-2,4-bis(phenylhydrazono)cyclohexane-1-carboxylic acid (4), 2-oxo-1,3-bis(phenylhydrazono)indan (5), and 2-oxo-1,3-bis(phenylhydrazono)propane (6) were studied by comparison of their n.m.r., u.v., visible, and i.r. spectra with the spectra of reference compounds of known structures. The results showed that compounds 1-6 exist in two forms. The red forms have an enolic (chelated) phenylhydrazono-phenylazo structure. A similarity of the compounds to the diphenylformazans is noted, and substantiated by a comparison of absorption spectra. Compound 2 crystallizes from aqueous ethyl alcohol in the form of a yellow hydrate shown to have a phenylhydrazono structure. On dehydration, the yellow hydrate yields the red enolic form.The n.m.r. spectra of 1,2,3-tris(phenylhydrazono) derivatives of cyclohexane, cyclopentane, and cyclohexanecarboxylic acid show two low-field signals indicative of two chelated rings. Tris(phenylhydrazono)propane in chloroform-d shows no low-field n.m.r. signals immediately after dissolution, but, after equilibration, shows a weak, low-field signal; this suggests that the substance may establish an equilibrium analogous to the equilibria reported by others for phenylosazones.

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