According to Wikipedia, vitamin C (ascorbic acid) "may also act as an antioxidant against oxidative stress," and is "widely used as a food additive, to prevent oxidation." But acids are, by definition, oxidizing agents, so how is it that ascorbic acid is used to prevent oxidation?
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2$\begingroup$ Most acids (except nitric and some others) have nothing to do with oxidation. Well, I mean, they may oxidize metals, but we are not made of metals. $\endgroup$– Ivan NeretinFeb 19, 2016 at 17:57
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1$\begingroup$ I dispute your claim that acids are oxidising agents. $\ce{HI}$ is a fairly strong acid that finds use as a reducing agent. $\endgroup$– bonFeb 19, 2016 at 19:25
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1 Answer
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Ascorbic acid is considered an antioxidant because it can supply an electron to a species with an unpaired electron (a "radical", labeled "X" in the below diagram) to stabilize the radical. Of course, since ascorbic acid has now lost an electron, it is itself a radical - but it is a very stable radical due to resonance. Below I have included a diagram of this process below, from UC Davis.
Note how the we can "electron-push" to get the unpaired electron in the middle structure to move to the oxygen on the other side of the ring. This resonance delocalization of the unpaired electron in the ascorbyl radical makes it much more favorable to have the unpaired electron in the ascorbyl radical rather than the X.
Because radicals normally poach electrons from surrounding molecules to pair with their lone electron, they normally cause a chain reaction where their "victim" goes on to pull electrons from another neighboring molecule (oxidation), and so on and so forth. However, because the ascorbyl radical is stable, it is less likely to poach an electron from another molecule in its environment, preventing the chain reaction from occurring. Thus, it is an antioxidant.
