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A strong acid readily donates a proton. Inductive effects and other factors can stabilize the negative charge of the conjugate base. The more stable the conjugate base, the more acidic the acid.

What I don't understand is that it seems to me that a more stable negative charge on the base will really hold onto the proton which is positive, yet the stronger the acid, the more readily it lets the proton go.

Can anyone explain this?


If you look at the resonating structure question (above on this page) and leave out the part of this question about "negative charge" and focus on "stability" I think you will have your answer. The more stable the conjugate base the stronger the acid. But that is just reasonable. I may have put words in your mouth; i.e. the answer to this question may not be the question you asked (you may have wanted to leave in the part about stable negative charge). I don't have an answer for the stabilized negative charge. Simply, the anion is stabilized by resonance and the more strongly stabilized anion must lead to the conclusion that the acid is stronger.

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