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Issue 7, 2012
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Molecular recognition-based catalysis in nucleophilic aromatic substitution: a mechanistic study

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Abstract

Nucleophilic aromatic substitution for nitro-activated substrates in the presence of glymes and crown ethers is reported. The kinetic study reveals the many-sided nature of the polyether-catalyzed SNAr mechanism as well as the main features affecting the course of the reaction. Thus, the process can be efficiently controlled by the catalyst through a molecular-recognition process, being also strongly dependent on the electronic structure of the substrate and, therefore, giving rise to a versatile reaction system. The kinetic model proposed herein allows quantifying the fractions of reaction proceeding through the different routes. Information on the nature of the host–guest interaction between the catalyst and the substrate will also be extracted.

Graphical abstract: Molecular recognition-based catalysis in nucleophilic aromatic substitution: a mechanistic study

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Publication details

The article was received on 21 Feb 2012, accepted on 24 Apr 2012, published on 27 Apr 2012 and first published online on 27 Apr 2012


Article type: Paper
DOI: 10.1039/C2NJ40128B
Citation: New J. Chem., 2012,36, 1519-1526
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    Molecular recognition-based catalysis in nucleophilic aromatic substitution: a mechanistic study

    N. Basilio, L. García-Río, Á. Peña-Gallego and M. Pérez-Lorenzo, New J. Chem., 2012, 36, 1519
    DOI: 10.1039/C2NJ40128B

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