Superacid

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A superacid is an acid with an acidity greater than that of 100% sulfuric acid. Commercially available superacids include trifluoromethanesulfonic acid (CF3SO3H), also known as triflic acid, and fluorosulfuric acid (FSO3H), both of which are about a thousand times stronger than sulfuric acid. The strongest superacids are prepared by the combination of two components, a strong Lewis acid and a strong Brønsted acid.

The term superacid was originally coined by James Bryant Conant in 1927 to describe acids that were stronger than conventional mineral acids. George A. Olah was awarded the 1994 Nobel prize in chemistry for his investigations of superacids and their use in the direct observation of carbocations. Olah's "magic acid", so-named for its ability to attack hydrocarbons, is prepared by mixing antimony pentafluoride (SbF5) and fluorosulfuric acid.

The strongest superacid system, the so-called fluoroantimonic acid, is a combination of hydrogen fluoride and SbF5. In this system, HF releases its proton (H+) concomitant with the binding of F− by the antimony pentafluoride. The resulting anion (SbF6−) is both a very weak nucleophile and a very weak base. The proton effectively becomes "naked", which accounts for the system's extreme acidity. Fluoroantimonic acid is 1019 times stronger than 100% sulfuric acid.[1]

Olah showed that at 140 °C (284 °F), FSO3H-SbF5 will convert methane into the tertiary-butyl carbocation, a reaction that begins with the protonation of methane:[2]

CH4 + H+ → CH5+
CH5+ → CH3+ + H2
CH3+ + 3 CH4 → (CH3)3C+ + 3 H2

[edit] See also

[edit] References

N. F. Hall and J. B. Conant, J. Am. Chem. Soc. 49, 3047, 1927.

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  1. ^ Olah, George A. (2005). "Crossing Conventional Boundaries in Half a Century of Research". Journal of Organic Chemistry 70 (7): 2413–2429. DOI:S0022-3263(04)00285-3 10.1021/jo040285o S0022-3263(04)00285-3. 
  2. ^ Olah, G. A.; Schlosberg, R. H. "Chemistry in Super Acids. I. Hydrogen Exchange and Polycondensation of Methane and Alkanes in FSO3H-SbF5 ("Magic Acid") Solution. Protonation of Alkanes and the Intermediacy of CH5+ and Related Hydrocarbon Ions. The High Chemical Reactivity of "Paraffins" in Ionic Solution Reactions" Journal of the American Chemical Society, 1968, volume 90, pages 2726 - 2727; DOI: 10.1021/ja01012a066
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