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Aromatic nucleophilic substitution in nonionic alkylglucoside micelles

Whiddon, Christy LU ; Bunton, C A and Söderman, Olle LU (2004) In Journal of Colloid and Interface Science 278(2). p.461-464
Abstract
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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Aromatic nucleophilic substitution, Nonionic micelles, Sugar-based surfactants, Alkylglucosides
in
Journal of Colloid and Interface Science
volume
278
issue
2
pages
461 - 464
publisher
Elsevier
external identifiers
  • wos:000224287100027
  • pmid:15450467
  • scopus:4344699076
ISSN
1095-7103
DOI
10.1016/j.jcis.2004.06.018
language
English
LU publication?
yes
id
74930a74-fd0c-4f9f-81bd-427868ea4d9c (old id 154035)
date added to LUP
2007-07-12 14:22:48
date last changed
2017-07-02 03:33:24
@article{74930a74-fd0c-4f9f-81bd-427868ea4d9c,
  abstract     = {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.},
  author       = {Whiddon, Christy and Bunton, C A and Söderman, Olle},
  issn         = {1095-7103},
  keyword      = {Aromatic nucleophilic substitution,Nonionic micelles,Sugar-based surfactants,Alkylglucosides},
  language     = {eng},
  number       = {2},
  pages        = {461--464},
  publisher    = {Elsevier},
  series       = {Journal of Colloid and Interface Science},
  title        = {Aromatic nucleophilic substitution in nonionic alkylglucoside micelles},
  url          = {http://dx.doi.org/10.1016/j.jcis.2004.06.018},
  volume       = {278},
  year         = {2004},
}