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Issue 31, 2018
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Size-dependent rate acceleration in the silylation of secondary alcohols: the bigger the faster

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Abstract

Relative rates for the reaction of secondary alcohols carrying large aromatic moieties with silyl chlorides carrying equally large substituents have been determined in organic solvents. Introducing thoroughly matching pairs of big dispersion energy donor (DED) groups enhanced rate constants up to four times, notably depending on the hydrogen bond donor ability of the solvent. A linear correlation between computed dispersion energy contributions to the stability of the silyl ether products and experimental relative rate constants was found. These results indicate a cooperation between solvophobic effects and DED-groups in the kinetic control of silylation reactions.

Graphical abstract: Size-dependent rate acceleration in the silylation of secondary alcohols: the bigger the faster

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Publication details

The article was received on 25 Apr 2018, accepted on 27 Jun 2018 and first published on 29 Jun 2018


Article type: Edge Article
DOI: 10.1039/C8SC01889H
Chem. Sci., 2018,9, 6509-6515
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Size-dependent rate acceleration in the silylation of secondary alcohols: the bigger the faster

    M. Marin-Luna, B. Pölloth, F. Zott and H. Zipse, Chem. Sci., 2018, 9, 6509
    DOI: 10.1039/C8SC01889H

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