Methane
Acid–base reactions

Like other hydrocarbons, methane is an extremely weak acid. Its p K in DMSO is estimated to be 56. It cannot be deprotonated in solution, but the conjugate base is known in forms such as methyllithium.

A variety of positive ions derived from methane have been observed, mostly as unstable species in low-pressure gas mixtures. These include methenium or methyl cation CH + 3, methane cation CH + 4, and methanium or protonated methane CH + 5. Some of these have been detected in outer space. Methanium can also be produced as diluted solutions from methane with superacids. Cations with higher charge, such as CH 2+ 6 and CH 3+ 7, have been studied theoretically and conjectured to be stable.

Despite the strength of its C–H bonds, there is intense interest in catalysts that facilitate C–H bond activation in methane (and other lower numbered alkanes).
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