THE FORMATION OF THE HYDRAZONE TAUTOMER IN HIGH RATIO DURING THE SYNTHESIS OF 4-(9-ANTHRYLAZO)-1-NAPHTHOL
RAMADAN ALI BAWA *
Department of Chemistry, Faculty of Science, Misurata University, P.O.Box 875, Misurata, Libya.
EBTISAM MOHAMMED ALZARAIDE
Department of Chemistry, Faculty of Science, Misurata University, P.O.Box 875, Misurata, Libya.
*Author to whom correspondence should be addressed.
Abstract
A mixture of two tautomers was found to be formed throughout the synthesis of the phenolic azo dye that is consisting of an anthracene moiety. The coupling reaction between the 9-anthryl diazonium bisulphate and the 1-naphthol yielded a 58% of a mixture of the azo phenol tautomer and its hydrazone counterpart. The spectroscopic data from the IR and NMR revealed the existence of these two tautomers. The tautomeric ratio was found to be of (1:4.5).
Keywords: Tautomers, azo dye, hydrazone, ratio