NMR Study of the Hydrogen Bonding of Sterically Hindered Phenols with Alicyclic Ethers and Pyridine

In a preliminary report¹ it was shown that the hydrogen-bond chemical shift, δ_AB, correlates with the change in enthalpy, δH, in the interaction of chloroform with a series of closely related oxygen and nitrogen bases. In this communication, we report the hydrogen bonding parameters for the interaction in cyclohexane medium between 2,4,6-tri-t-butylphenol and tetrahydrofuran, tetrahydropyran and pyridine, and between 2,6-di-1-adamantyl-4-t-butylphenol and pyridine. There is correlation between the δ_AB and δ_AE for the same proton donor (2,4,6-tri-t-butylphenol) and the closely related alicyclic bases, and for the same base (pyridine) and the two closely related sterically hindered phenols. The temperature dependence of the δ_AB in these systems is also reported.