Molecular “Pincer” from a Diimidazolium Salt: A Study of Binding Ability

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Abstract

The anion recognition ability of the dicationic imidazolium salt 3,3′-di-n-octyl-1,1′-(1,3-phenylenedimethylene)diimidazolium 1,5-naphthalenedisulfonate ([m-Xyl-(oim)2][1,5-NDS])was investigated in acetonitrile solution by means of proton NMR titrations. A wide range of anions,comprising simple inorganic ions, halides, and mono- and dicarboxylates was taken into account. Thestudy showed that this receptor binds carboxylate anions more strongly than halides. Moreover [m-Xyl-(oim)2][1,5-NDS] displays selectivity for di- over monocarboxylate anions. The complexstability was mainly affected by the anion basicity in the presence of monocarboxylates, whereas theflexibility of the alkyl chain linking the two carboxylate moieties appeared to play a major role in thepresence of dicarboxylate anions.
Lingua originaleEnglish
pagine (da-a)10203-10208
Numero di pagine6
RivistaJournal of Organic Chemistry
Volume78
Stato di pubblicazionePublished - 2013

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Anions
Salts
Alkalinity
Titration
Protons
Display devices
Nuclear magnetic resonance
Ions
diazonaphthalenedisulfonic acid

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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title = "Molecular “Pincer” from a Diimidazolium Salt: A Study of Binding Ability",
abstract = "The anion recognition ability of the dicationic imidazolium salt 3,3′-di-n-octyl-1,1′-(1,3-phenylenedimethylene)diimidazolium 1,5-naphthalenedisulfonate ([m-Xyl-(oim)2][1,5-NDS])was investigated in acetonitrile solution by means of proton NMR titrations. A wide range of anions,comprising simple inorganic ions, halides, and mono- and dicarboxylates was taken into account. Thestudy showed that this receptor binds carboxylate anions more strongly than halides. Moreover [m-Xyl-(oim)2][1,5-NDS] displays selectivity for di- over monocarboxylate anions. The complexstability was mainly affected by the anion basicity in the presence of monocarboxylates, whereas theflexibility of the alkyl chain linking the two carboxylate moieties appeared to play a major role in thepresence of dicarboxylate anions.",
author = "Salvatore Marullo and Francesca D'Anna and Renato Noto",
year = "2013",
language = "English",
volume = "78",
pages = "10203--10208",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",

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TY - JOUR

T1 - Molecular “Pincer” from a Diimidazolium Salt: A Study of Binding Ability

AU - Marullo, Salvatore

AU - D'Anna, Francesca

AU - Noto, Renato

PY - 2013

Y1 - 2013

N2 - The anion recognition ability of the dicationic imidazolium salt 3,3′-di-n-octyl-1,1′-(1,3-phenylenedimethylene)diimidazolium 1,5-naphthalenedisulfonate ([m-Xyl-(oim)2][1,5-NDS])was investigated in acetonitrile solution by means of proton NMR titrations. A wide range of anions,comprising simple inorganic ions, halides, and mono- and dicarboxylates was taken into account. Thestudy showed that this receptor binds carboxylate anions more strongly than halides. Moreover [m-Xyl-(oim)2][1,5-NDS] displays selectivity for di- over monocarboxylate anions. The complexstability was mainly affected by the anion basicity in the presence of monocarboxylates, whereas theflexibility of the alkyl chain linking the two carboxylate moieties appeared to play a major role in thepresence of dicarboxylate anions.

AB - The anion recognition ability of the dicationic imidazolium salt 3,3′-di-n-octyl-1,1′-(1,3-phenylenedimethylene)diimidazolium 1,5-naphthalenedisulfonate ([m-Xyl-(oim)2][1,5-NDS])was investigated in acetonitrile solution by means of proton NMR titrations. A wide range of anions,comprising simple inorganic ions, halides, and mono- and dicarboxylates was taken into account. Thestudy showed that this receptor binds carboxylate anions more strongly than halides. Moreover [m-Xyl-(oim)2][1,5-NDS] displays selectivity for di- over monocarboxylate anions. The complexstability was mainly affected by the anion basicity in the presence of monocarboxylates, whereas theflexibility of the alkyl chain linking the two carboxylate moieties appeared to play a major role in thepresence of dicarboxylate anions.

UR - http://hdl.handle.net/10447/84226

M3 - Article

VL - 78

SP - 10203

EP - 10208

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

ER -