Protonation of Phenyl(trimethylsilyl)acetylene: A Surprisingly Weak Stabilization of a Carbocation by a β‐Trimethylsilyl Group | Zendy

Kresge A. Jerry | Zendy; Tobin John B. | Zendy

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Protonation of Phenyl(trimethylsilyl)acetylene: A Surprisingly Weak Stabilization of a Carbocation by a β‐Trimethylsilyl Group

Author(s) -

Kresge A. Jerry,

Tobin John B.

Publication year - 1993

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199307211

Subject(s) - carbocation , trimethylsilyl , phenylacetylene , protonation , chemistry , silylation , hyperconjugation , acetylene , medicinal chemistry , group (periodic table) , photochemistry , computational chemistry , organic chemistry , catalysis , molecule , ion

The protodesilylation of the title compound 1 [Eq. (a)] proceeds via the vinyl cation 2 , whose stabilization by the β‐trimethylsilyl group is much smaller than expected. The comparison of the rate of protonation of 1 and that of phenylacetylene gives a small β‐silyl stabilizing effect (ΔΔ G † = 3.4 kcal mol −1 ). This surprising result is explained by insufficient hyperconjugation.

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