ACIDITY OF ALKYL SUBSTITUTED ALCOHOLS - ARE ALKYL-GROUPS ELECTRON-DONATING OR ELECTRON-WITHDRAWING

Two important functional group properties, the group electronegativity and hardness, are calculated for a number of alkyl groups. The results indicate that alkyl groups become less electronegative and hard with increasing group size. The calculated properties are used in a study of the inversion of the alkyl alcohol acidity scale when going from aqueous solution to the gas phase. Finally, the Sanderson electronegativity equalization principle using functional group properties is shown to be a valuable tool in describing the charge distribution of these molecular systems.