Gitonic Geminal Superelectrophiles

Superelectrophiles and Their Chemistry, by George A. Olah and Douglas A. Klumpp Copyright 2008 John Wiley Sons, Inc. 

The ab initio calculations determined the C3, structure to be a kinetically stable minimum. 

Varied one carbon geminal dications have been generated in the gas-phase and studied by theoretical methods. For example, mass spectroscopic studies of methane have detected dicationic species, CH42+, CH3 2+, CH22+, and CH 2+, while other studies have examined the structures of halogenated one carbon geminal dications.13 The halogenated systems 

The gold complexes were characterized by X-ray crystallography and represent isolobal analogs of L 02+. 

Weaker acids do not catalyze the methylation. Despite that trialkyloxonium ions have a formal positive charge, the oxygen atom can still act as a Lewis base resulting in an interaction between the lone pair electrons on the oxygen and the highly acidic protosolvating system. 

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