Desilylation of β-silyl pyridinium ions: Gas-phase and solution-phase studies in conjunction with DFT calculations

Organometallics

Volumn 28, Issue 15, 2009, Pages 4276-4282

  Karnezis, Asimo ^a   O'Hair, Richard A J ^a   White, Jonathan M ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENIUM ION; COMPUTATIONAL STUDIES; CONDENSED PHASE; DESILYLATION; DEUTERATED DERIVATIVES; DFT CALCULATION; ENAMINE INTERMEDIATES; GAS PHASE CHEMISTRY; GASPHASE; HYDRIDE ABSTRACTION; HYDRIDE TRANSFERS; ION-MOLECULE COMPLEXES; PYRIDINIUM; SEALED TUBES; TANDEM MASS SPECTROMETRY; TRIFLATES;

DEUTERIUM; ELECTROSPRAY IONIZATION; IONIZATION OF GASES; MASS SPECTROMETRY; MOLECULAR VIBRATIONS; PHASE EQUILIBRIA; PROTON TRANSFER; SILANES; SILICON; SUGAR (SUCROSE); SULFUR COMPOUNDS;

IONS;

EID: 68149156286     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900117w     Document Type: Article

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27. A referee made the suggestion that a concerted mechanism via a N-coordinated trimethylsilyl cation complex might be involved for both the proton transfer and hydride transfer pathways for the 2-substituted derivative 20. While the N-coordinated species was indeed located as a local minimum 168 kJ/mol above the cation 20, attempts to locate a transition state leading to 34 or 36 resulted in the location of the ionmolecule complex. The Gaussian archive for this species is included in the Supporting Information.