In situ sulfonation of alkyl benzene self-assembled monolayers : product distribution and kinetic analysis
The sulfonation of aromatic rings held at the surface of a covalently anchored self-assembled monolayer has been analyzed in terms of the rates and isomer distribution of the sulfonation process. The observed product distributions are similar to those observed in solution, though the data obtained s...
| Publié dans: | Langmuir : the ACS journal of surfaces and colloids. - 1985. - 24(2008), 19 vom: 07. Okt., Seite 10910-9 |
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| Auteur principal: | |
| Autres auteurs: | , |
| Format: | Article en ligne |
| Langue: | English |
| Publié: |
2008
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| Accès à la collection: | Langmuir : the ACS journal of surfaces and colloids |
| Sujets: | Journal Article Research Support, Non-U.S. Gov't Sulfones Toluene 3FPU23BG52 Benzene J64922108F |
| Résumé: | The sulfonation of aromatic rings held at the surface of a covalently anchored self-assembled monolayer has been analyzed in terms of the rates and isomer distribution of the sulfonation process. The observed product distributions are similar to those observed in solution, though the data obtained suggest that the reaction rate and the ortho/para product ratio depend on the length of the tether anchoring the aryl ring to the monolayer interface. It was also found that the interface becomes progressively more disordered and the observed reaction rates decrease as the reaction progresses. There is no evidence for a bias in favor of reaction at the more exposed para-position nor is there evidence for an enhanced reaction rate due to the increased disorder and/or improved wetting as the reaction proceeds. This is the first detailed study of electrophilic aromatic substitution at a monolayer interface. It introduces new approaches to the spectroscopic analysis of reactions on self-assembled monolayers and provides a new general approach to the analysis of isomeric product distribution in such a setting |
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| Description: | Date Completed 28.10.2008 Date Revised 21.11.2013 published: Print-Electronic Citation Status MEDLINE |
| ISSN: | 1520-5827 |
| DOI: | 10.1021/la800746k |