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2-(2-Hydroxyphenyl)benzotriazoles. I. Synthesis ad their ultraviolet and infrared spectra

J. Běluša, Z. Janoušek, and H. Knoflíčková

Department of Organic Chemistry, Faculty of Natural Sciences, J. E. Purkyně University, 611 37 Brno


Abstract:  2-(2-Hydroxy-5-X-phenyl)-5-Y-benzotriazoles were prepared by reduction of the corresponding o-nitroazo compounds. The shifts of wavenumbers of the stretching vibrations of O—H group forming intramolecular hydrogen bond with nitrogen of the triazole ring were linearly dependent on the Hammett σR constants of the substituents X (ρ = —61) and Y (ρ = +45). The shifts of wavenumbers of the absorption band in the region of 30 200 —25 600 cm-1 with the σR  constants of the groups X (ρ = +5.1) fulfilled this correlation, too. Also the logarithm of molar absorptivity of the absorption band at about 300 nm was nearly linearly dependent on the σR   constants of the groups Y as well as that of the band in the region of 330 — 390 nm on the σR constants of the groups X.

Full paper in Portable Document Format: 285a673.pdf


Chemical Papers 28 (5) 673–679 (1974)

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