Is the Perfluorinated Trityl Cation Worth a Revisit? A Theoretical Study on the Lewis Acidities and Stabilities of Highly Halogenated Trityl Derivatives

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Couchman, S. A., Wilson, D. J., & Dutton, J. L. (2014). Is the perfluorinated trityl cation worth a revisit? A theoretical study on the lewis acidities and stabilities of highly halogenated trityl derivatives. European Journal of Organic Chemistry, 2014(18), 3902-3908. doi:10.1002/ejoc.201402263



030701 Quantum Chemistry


The relative Lewis acidities of a series of known, unknown and observed but unstable halogenated derivatives of the trityl cation have been probed in a computational study. The Lewis acidity was investigated from hydride, fluoride and methide affinities. The results indicate that the perhalogen-ated trityl cation [C(C6F5)3]+ is a desirable synthetic target, especially in the modern age of weakly coordinating anions. Our results also indicate that the stable [C(C6Cl5)3]+ cation may be an equally interesting Lewis acid.


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At the time of writing David Wilson was affiliated with Avondale College as a Conjoint Lecturer.