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Issue 1, 2017
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Aromatic sulfonation with sulfur trioxide: mechanism and kinetic model

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Abstract

Electrophilic aromatic sulfonation of benzene with sulfur trioxide is studied with ab initio molecular dynamics simulations in gas phase, and in explicit noncomplexing (CCl3F) and complexing (CH3NO2) solvent models. We investigate different possible reaction pathways, the number of SO3 molecules participating in the reaction, and the influence of the solvent. Our simulations confirm the existence of a low-energy concerted pathway with formation of a cyclic transition state with two SO3 molecules. Based on the simulation results, we propose a sequence of elementary reaction steps and a kinetic model compatible with experimental data. Furthermore, a new alternative reaction pathway is proposed in complexing solvent, involving two SO3 and one CH3NO2.

Graphical abstract: Aromatic sulfonation with sulfur trioxide: mechanism and kinetic model

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Publication details

The article was received on 05 Aug 2016, accepted on 10 Sep 2016 and first published on 12 Sep 2016


Article type: Edge Article
DOI: 10.1039/C6SC03500K
Citation: Chem. Sci., 2017,8, 680-688
  • Open access: Creative Commons BY-NC license
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    Aromatic sulfonation with sulfur trioxide: mechanism and kinetic model

    S. L. C. Moors, X. Deraet, G. Van Assche, P. Geerlings and F. De Proft, Chem. Sci., 2017, 8, 680
    DOI: 10.1039/C6SC03500K

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