CONTRIBUTION CONCERNING THE PROBLEM OF THE INTRAMOLECULAR HYDROGEN BONDS IN ORTHO HALOPHENOLS

Abstract

The infrared spectra of the four ortho halophenols were measured in carbon tetrachloride solutions containing variable amounts of ether. The integrated intensities of the stretching band corresponding to the intermolecularly hydrogen-bonded OH groups were determined and plotted against ether concentration. From the curves obtained in this manner it was possible to deduce the relative strengths of the intramolecular hydrogen bonds which are present in these molecules. They are, in order of increasing strength: F < I < Br < Cl. This result is compared to others, published in the literature, obtained using alternative methods.