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Aromatic nucleophilic substitution in nonionic alkylglucoside micelles

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Author

Summary, in English

The kinetics and mechanism of the aromatic nucleophilic substitution reaction of 2,4-dinitrochlorobenzene (DNCB) with OH- in nonionic sugar-derived micelles were investigated and compared with those for reaction in polyoxyethylene glycol surfactants. Hydroxyl groups on the sugar headgroups of micellized n-nonyl beta-D-glucopyranoside (C(9)G(1)), n-dodecyl beta-D-maltoside (C(12)G(2)), and n-dodecyl beta-D-maltotrioside (C(12)G(3)) are partially deprotonated by OH- and the alkoxide ions react with DNCB, forming an arene ether. Observation of more than one isosbestic point indicates that more than one intermediate ether is formed, largely at C3 or C4 with micellar stereocontrol. Over time the ethers react with OH- giving 2,4-dinitrophenoxide ion. (C) 2004 Elsevier Inc. All rights reserved.

Department/s

Publishing year

2004

Language

English

Pages

461-464

Publication/Series

Journal of Colloid and Interface Science

Volume

278

Issue

2

Document type

Journal article

Publisher

Elsevier

Topic

  • Physical Chemistry

Keywords

  • Aromatic nucleophilic substitution
  • Nonionic micelles
  • Sugar-based surfactants
  • Alkylglucosides

Status

Published

ISBN/ISSN/Other

  • ISSN: 1095-7103