(E)-2-Acetyl-4-[(3-methylphenyl)diazenyl]phenol: an X-ray and DFT study

Abstract

The title compound, C15H14N2O2, an azo dye, displays a trans configuration with respect to the N=N bridge. The dihedral angle between the aromatic rings is 0.18 (14)°. There is a strong intra­molecular O—H⋯O hydrogen bond. Geometrical parameters, determined using X-ray diffraction techniques, are compared with those calculated by density functional theory (DFT), using hybrid exchange–correlation functional, B3LYP and semi-empirical (PM3) methods.

1-[(E)-2-(5-tert-Butyl-2-hydroxyphenyl)diazen-1-yl]naphthalen-2-ol

“…In the title compound, N-N bond lengths are 1.287 Å for N1-N2 , between the suggested N=N double bond and N-N single bond lengths. In the molecule, all bond lengths are in good agreement with those reported for other azo compounds (Yazıcı et al, 2010;Karadayı et al, 2006). We report here in the crystal structure of the title compound, obtained through the diazotization of 4-tert-butyl-2-hydroxy aniline followed by a coupling reaction with 2-naphthol.…”

“…For general background to azo compounds and their use in dyes, pigments and advanced materials, see: Lee et al (2004). For related azo compounds, see: Yazıcı et al (2010); Karadayı et al (2006); Oakes (2002); Olivieri et al (1989). For the synthesis, see: Wang et al (2003).…”