ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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)