THE INFRARED FREQUENCIES AND INTENSITIES OF THE HYDROXYL BAND IN ORTHO-SUBSTITUTED PHENOLS

Abstract

The infrared frequencies, intensities, and half-band widths of the fundamental stretching vibration of the hydroxyl group have been measured for a large number of ortho-alkyl phenols. It has been found that phenols containing a single ortho-alkyl substituent exist as cis and trans isomers in unequal amounts, the trans isomer being the more abundant. The difference in free energy between the two isomers in dilute solution in carbon tetrachloride at 24 °C has been measured for ortho-cresol, 2,3-dimethyl phenol, and several ortho-tert-alkyl phenols.