C–F⋯HO hydrogen bond in 8-fluoro-4-methyl-1-naphthol

The 8-fluoro-4-methyl-1-naphthol forms the intermolecular bifurcated HB, OH⋯(F, HO) in the crystal. This is quite contrasting to the reported results of the ab initio calculations. On the contrary, the intramolecular hydrogen bond in solution was confirmed by 1H, 13C, and 19F NMR spectra.

Graphical abstractThe C–F⋯HO hydrogen bond of 8-fluoro-4-methyl-1-naphthol was observed in the crystal and in solution. It forms the intermolecular bifurcated HB in the crystal and the intramolecular hydrogen bond in solution was confirmed by 1H, 13C, and 19F NMR spectra.Figure optionsDownload full-size imageDownload as PowerPoint slide