Title

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

Author Faculty (Discipline)

Science

Document Type

Article

Publication Date

6-10-2014

Early Online Version

5-6-2014

Journal

European Journal of Organic Chemistry

Volume Number

2014

Issue Number

18

Page Numbers

3902-3908

ISSN

1434-193X

Embargo Period

3-29-2015

ANZSRC / FoR Code

030701 Quantum Chemistry

Peer Review

Before publication

Abstract

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.

Link to publisher version (DOI)

https://doi.org/10.1002/ejoc.201402263

Comments

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