Triphenylmethanol

Triphenylmethanol is an organic compound with the chemical formula C(C6H5)3OH. It is a molecule of methanol where the non-alcoholic hydrogen atoms have been replaced by phenyl functional groups. It is an ingredient in a type of dye called triarylmethane dyes.

It is more basic than other alcohols. Protonation by a strong acid happens on the oxygen atom, and is followed by elimination of a water molecule. This leaves the very stable trityl cation, a carbocation with a positive charge on the central carbon atom.

Triphenylmethanol was important to the discovery of carbocations. A solution of triphenylmethanol and sulfuric acid, two colorless chemicals, turns bright yellow. Adolf von Baeyer saw that this solution contained a salt-like chemical, now known as trityl bisulfate. von Baeyer named the tendency for organic compounds like triphenylmethanol to make colored salts "halochromy".[1]


References

  1. ↑ George A. Olah (1994-12-08). "Nobel Lecture: My Search for Carbocations and their Role in Chemistry" (PDF). Nobel Foundation. Retrieved 2025-04-23.
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