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A number of studies have been made on the frequency shifts that occur when phenol is dissolved in dioxan. Many of these have attempted to attribute shifts in 0-H stretching frequency to hydrogen bond association between phenol and dioxan. This approach is illustrated by the studies of Freymann,l Gordy and Nie l~en ,~ and Lin~leberg.~ Hydrogen bond association of phenol and dioxan in carbon tetrachloride was studied from infrared spectra by Flett,4 T ~ u b o i , ~ and Allerhand and Schleyer.6 Flett evaluated free energies and heats of formation of hydrogen bonds between phenol and dioxan, while Tsuboi estimated the dissociation energy of intermolecular hydrogen bonds between proton donor (phenol) and proton acceptor (dioxan). Allerhand and Schleyer studied the variation of frequency shift due to change in concentration of dioxan. I t appears that no systematic study has been made so far about the effect of the substituent in the proton donor on the frequency shift. The present study was taken up with a view to examine the substitute effect on frequency shift due to hydrogen bond formation between substituted phenols and dioxan.

Infrared spectroscopic study of hydrogen bonding: Hydrogen bond association of phenols with dioxan