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

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 σ_R 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 σ_R  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 σ_R   constants of the groups Y as well as that of the band in the region of 330 — 390 nm on the σ_R constants of the groups X.

Full paper in Portable Document Format: 285a673.pdf

Chemical Papers 28 (5) 673–679 (1974)