AN INVESTIGATION OF HYDROGEN BONDING CHARACTERISTICS OF BUTANEDIOLS

The infrared spectra of 1,2, 1,3, 2,3, and 1,4 butanediols have been measured in the vapor phase, as pure liquids and as dilute solutions in CCl4 and CS2. Temperatures were varied from ambient to 300°C. As pure liquids, the spectroscopic behavior of these compounds is indistinguishable from that of monofunctional alcohols. ΔH's of intramolecular hydrogen bond formation were found to be -0.75 kcal mole for the 1,2 and 2,3 diols; -1.35 kcal mole for 1,3 diol and -3.00 kcal mole for 1,4 diol, all in the vapor phase. Band overlap reduces the reliability of the ΔH's for the 1,2 and 2,3 diols. The values were about 30% lower in solution. Conclusions are presented regarding the relative importance of geometrical factors and solventsolute interactions on frequency shifts and on ΔH's. © 1969.