Aromatic nucleophilic substitution in nonionic alkylglucoside micelles
(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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/154035
- author
- Whiddon, Christy LU ; Bunton, C A and Söderman, Olle LU
- organization
- publishing date
- 2004
- 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
- 2016-04-01 11:52:49
- date last changed
- 2022-04-05 06:28:31
@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}},
keywords = {{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}},
doi = {{10.1016/j.jcis.2004.06.018}},
volume = {{278}},
year = {{2004}},
}