Three isomeric forms of hydroxyphenyl-2-oxazoline: 2-(2-hydroxyphenyl)-2-oxazoline, 2-(3-hydroxyphenyl)-2-oxazoline and 2-(4-hydroxyphenyl)-2-oxazoline

Artikel i vetenskaplig tidskrift, 2005

Crystal structures are reported for three isomeric compounds, namely 2-(2-hydroxyphenyl)-2-oxazoline, (I), 2-(3-hydroxyphenyl)-2-oxazoline, (II), and 2-(4-hydroxyphenyl)-2-oxazoline, (III), all C9H9NO2 [systematic names: 2-(4,5-dihydro-1,3-oxazol-2-yl)phenol, (I), 3-(4,5-dihydro-1,3-oxazol-2-yl)phenol, (II), and 4-(4,5-dihydro-1,3-oxazol-2-yl)phenol, (III)]. In these compounds, the deviation from coplanarity of the oxazoline and benzene rings is dependent on the position of the hydroxy group on the benzene ring. The coplanar arrangement in (I) is stabilized by a strong intramolecular O-H...N hydrogen bond. Surprisingly, the 2-oxazoline ring in molecule B of (II) adopts a 3T4 (C2TC3) conformation, while the 2-oxazoline ring in molecule A, as well as that in (I) and (III), is nearly planar, as expected. Tetramers of molecules of (II) are formed and they are bound together via weak C-H...N hydrogen bonds. In (III), strong intermolecular O-H...N hydrogen bonds and weak intramolecular C-H...O hydrogen bonds lead to the formation of an infinite chain of molecules perpendicular to the b direction. This paper also reports a theoretical investigation of hydrogen bonds, based on density functional theory (DFT) employing periodic boundary conditions.