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Infrared Spectra of Some Substituted Monoazobenzenes, Hydroxyhydrazone Tautornerism in Orthohydroxy, and Orthoarninoazobenzenes

Volume 36, Number 6 (Dec. 1982) Page 682-684

Afifi, M.S.; Tera, F.M.; Sayed, A.M.B.

The infrared spectra of substituted monoazobenzenes (O-Cl, m-Cl, p-Cl, p-Br, 2,5-dichloro, O-NO2, m-No2, p-NO2, and 2,4-dinitro) derived from p-hydroxy, O-aminobenzenes (series A), and of the substituted monoazobenzenes (O-Cl, m-Cl, p-Cl, 2,5-dichloro, p-Br, and O-NO2) derived from p-amino, O-hydroxybenzene (series B) have been recorded and tentatively assigned. In series A the O-NO2, m-NO2, and 2,4-dinitro compounds and all members of series B show a relatively intense IR band at 1651 ± 17 cm-1. The appearance of this band in the nitrocompounds of series A at 1654 ± 14 cm-1 is interpreted as being probably due to coupling of δNH2 and α as NO2. The band at 1642 ± 8 cm-1 in series B is tentatively as signed as a v C==O absorption. This interpretation is regarded as evidence of tautomeric equilibrium in series B of these azodyes.