Theoretical Gas‐Phase Stabilities of α‐Trimethylsilyl‐Substituted Tertiary Carbenium Ions | Zendy

Grunenberg Jörg | Zendy; Laschat Sabine | Zendy; Dickner Tim | Zendy

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Theoretical Gas‐Phase Stabilities of α‐Trimethylsilyl‐Substituted Tertiary Carbenium Ions

Author(s) -

Grunenberg Jörg,

Laschat Sabine,

Dickner Tim

Publication year - 2003

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200300273

Subject(s) - chemistry , trimethylsilyl , hyperconjugation , hydride , gas phase , ion , group (periodic table) , carbocation , methyl group , medicinal chemistry , carbenium ion , computational chemistry , organic chemistry , inorganic chemistry , hydrogen , molecule

Theoretical hydride ion affinities in the gas phase are presented for α‐SiMe 3 ‐substituted tertiary carbenium ions. Thermodynamic stabilization of the ”nascent“ ions by a single trimethylsilyl group is weaker than by a tert ‐butyl group but comparable to the effect of a methyl group. In the case of the cyclopropenylium cation, the stabilization by a trimethylsilyl group even exceeds the effectiveness of a tert ‐butyl group. Compliance constants are used to quantify the chemical concept of hyperconjugation. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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