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The structure of o-aminoazo compounds

K. Antoš and Š. Kováč

Slovak Technical University, Bratislava


Abstract: From the analyses of infrared absorption spectra, 3200-3600 cm-1, amino derivs. of dimethylaminoazobenzene were identified. Free amino groups, capable of reacting with CSCl2, show 2 absorption bands of N-H bonds in NH2 groups in the area 3410 cm-1 (symmetric valence vibration) and in the area 3500 cm-1 (asymmetric valence vibration). In this group are m- and p-amino derivs. and the 2-amino-3-methyl deriv., which is the only one reacting with CSCl2. The other o-amino derivs. (assumed cis forms) show 3 absorption bands in the area 3310, 3400, and 3490 cm-1 The first one is the result of the effect of H bonds of the amino groups, indicating 5-member rings (which are the cause of the non-reactivity of the NH2 group with CSCl2). The assumed bands forms do not give in the infrared spectra the absorption bands of amino groups, which indicates a quinoid structure showing a wide absorption band in the area 3450 cm-1 These are benzotriazole derivs., not capable of reaction with CSCl2.

Full paper in Portable Document Format: 163a187.pdf (in Slovak)


Chemical Papers 16 (3) 187–199 (1962)

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