Abstract

The infrared spectra of substituted monoazobenzenes (<i>O</i>-Cl, <i>m</i>-Cl, <i>p</i>-Cl, <i>p</i>-Br, 2,5-dichloro, <i>O</i>-NO₂, <i>m</i>-No₂, <i>p</i>-NO₂, and 2,4-dinitro) derived from <i>p</i>-hydroxy, <i>O</i>-aminobenzenes (series A), and of the substituted monoazobenzenes (<i>O</i>-Cl, <i>m</i>-Cl, <i>p</i>-Cl, 2,5-dichloro, <i>p</i>-Br, and <i>O</i>-NO₂) derived from <i>p</i>-amino, <i>O</i>-hydroxybenzene (series B) have been recorded and tentatively assigned. In series A the <i>O</i>-NO₂, <i>m</i>-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 <i>v</i> C==O absorption. This interpretation is regarded as evidence of tautomeric equilibrium in series B of these azodyes.

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