Abstract: | The hydroxyl proton chemical shift in substituted benzyl alcohols may be used, either at infinite dilution in CCl4, or in dilute solutions in DMSO, as a reliable indicator of substituent effects. The sensitivity of the hydroxyl proton to substituents is much greater than that of the methylene protons, and this is shown to be due to an increased dependence of the hydroxyl proton on the field effect of the substituent. The percent resonance contribution to the OH chemical shifts is identical in benzyl alcohols and phenols. |