Secondary Deuterium Isotope Effect in an Electrophilic Aromatic Substitution ‐ Protodesilylation of Trimethylphenylsilane | Zendy

Szele Ivanka | Zendy

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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.

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