PMID: 9539696Apr 29, 1998Paper

Attempted hydrogen-deuterium exchange of the protio-trimethyloxonium dication (CH3)3OH2+, study of methylating ability of (CH3)3O+ in superacids and theoretical investigations

Proceedings of the National Academy of Sciences of the United States of America
George A OlahG K Prakash

Abstract

Attempted hydrogen-deuterium exchange of trimethyloxonium ion, (CH3)3O+ with excess of 1:1 (2)HF/SbF5 superacid at -30 degreesC over a period of 30 days showed no exchange. Theoretical calculations at the MP2/6-31G** level are in accord with the lack of hydrogen-deuterium exchange in the methyl group of the (CH3)3O+ cation as protonation (protosolvation) prefers the oxygen lone pair of electrons, instead of a C---H bond. Methylation of aromatics with the (CH3)3O+CF3SO3- in CF3SO3H and 2CF3SO3H:B(O3SCF3)3 was also studied. Whereas in triflic acid no alkylation was observed, in triflatoboric acid, a powerful superacid, alkylation takes place, indicating protolytic activation of the trimethyloxonium ion.

References

Sep 1, 1986·Journal of the American Chemical Society·W KochD Cremer

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Citations

Dec 3, 2011·Journal of the American Chemical Society·Evgenii S StoyanovChristopher A Reed

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