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Secondary Deuterium Isotope Effect in an Electrophilic Aromatic Substitution ‐ Protodesilylation of Trimethylphenylsilane
Author(s) -
Szele Ivanka
Publication year - 1981
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19810640833
Subject(s) - chemistry , kinetic isotope effect , deuterium , methanol , electrophilic aromatic substitution , proton , aqueous solution , electrophile , silane , ion , isotope , medicinal chemistry , photochemistry , inorganic chemistry , organic chemistry , catalysis , physics , quantum mechanics
Reaction rates for the protodesilylation of trimethylphenylsilane and of [2,4,6‐ 2 H 3 ]‐trimethylphenylsilane by HCIO 4 , were measured in aqueous methanol (2:5, v/v ) and the secondary deuterium isotope effect for the reaction was found to be k H / k D3 = 0.79. The magnitude of the observed isotope effect supports a mechanism in which the rate‐determining step is the proton transfer from the hydronium ion to the silane to form a σ‐intermediate.