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The relative gas-phase acidities and basicities of alkyl-substituted amines,* 12 mercaptans,3 alcohols,2 and phenols4 have been shown to be strongly dominated by the charge-induced dipole stabilization of the ion formed by protonation or deprotonation (the substituent polarizability effect2). When the alkyl substituent is nonconjugated, the observed acidities or basicities relative to the unsubstituted (H) compound can be attributed approximately quantitatively to the polarizability effect since recent experimental5 and theoretical6 evidence indicates that no significant inductive effects are involved. For poorly solvated ions, the substituent

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