NDLI: Pyridinium/urea-based anion receptor: methine formation in the presence of basic anions

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Organic & Biomolecular Chemistry Vol -15

Organic & Biomolecular Chemistry Vol -9

Organic & Biomolecular Chemistry Vol - 9 Issue - 24

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Construction of a tunable metallohydrolase center on an invertible molecular pocket

An efficient copper-catalyzed synthesis of anilines by employing aqueous ammonia

CF₂-Containing acetylenephosphonates in heterocyclization reactions: the first synthesis of 2-difluoromethyl azaxanth-3-ylphosphonates

Functionalized 2,3-dihydrofurans via palladium-catalyzed oxyarylation of α-allyl-β-ketoesters

Thiacalix[4]arene based reconfigurable molecular switches: set-reset memorized sequential device

Naphthalene- and perylenediimides with hydroquinones, catechols, boronic esters and imines in the core

An organocatalytic approach to enantiomerically enriched α-arylcyclohexenones and cyclohexanones

4′-Alkoxy oligodeoxynucleotides: a novel class of RNA mimics

Tautomerism in Schiff bases. The cases of 2-hydroxy-1-naphthaldehyde and 1-hydroxy-2-naphthaldehyde investigated in solution and the solid state

Pyridinium/urea-based anion receptor: methine formation in the presence of basic anions

Versatile trifunctional chemosensor of rhodamine derivative for Zn²⁺, Cu²⁺ and His/Cys in aqueous solution and living cells

Synthesis and biological properties of conjugates between fluoroquinolones and a N3′′-functionalized pyochelin

Synthesis and biological evaluation of potential new inhibitors of the bacterial transferase MraY with a β-ketophosphonate structure

Cyclohexyl “base pairs” stabilize duplexes and intensify pyrene fluorescence by shielding it from natural base pairs

Sulfonamide carbazole receptors for anion recognition

One-pot near-ambient temperature syntheses of aryl(difluoroenol) derivatives from trifluoroethanol

Bis- and tris-naphthoimidazolium derivatives for the fluorescent recognition of ATP and GTP in 100% aqueous solution

Facile aromatic radiofluorination of [¹⁸F]flumazenil from diaryliodonium salts with evaluation of their stability and selectivity

Synthesis of a library of oligothiophenes and their utilization as fluorescent ligands for spectral assignment of protein aggregates

Exploring the synthetic potency of the first furanothioglycoligase through original remote activation

Three-component, one-pot sequential synthesis of glyco-hydantoin conjugates

A new practical synthesis of triaryl and trisindolylmethanes under solvent-free reaction conditions

Predicting Michael-acceptor reactivity and toxicity through quantum chemical transition-state calculations

Divergent synthetic approach to 6′′-modified α-GalCer analogues

An efficient strategy for the general synthesis of 3-aryl substituted pyrazolo[5,1-c][1,4]benzoxazines and pyrazolo[1,5-a][1,4]benzodiazepin-6(4H)-ones

Highly efficient aldol additions of DHA and DHAP to N-Cbz-amino aldehydes catalyzed by l-rhamnulose-1-phosphate and l-fuculose-1-phosphate aldolases in aqueous borate buffer

Thiazolium-catalyzed intermolecular Stetter reaction of linear and cyclic alkyl α-diketones

The reactivity of quaternary ammonium- versus potassium- fluorides supported on metal oxides: paving the way to an instantaneous detoxification of chemical warfare agents

Highly diastereoselective Friedel–Crafts reaction of arenes with N-tert-butanesulfinylimino ester towards the efficient synthesis of α-arylglycines

A new cyclopamine glucuronide prodrug with improved kinetics of drug release

Synthesis of 1,2,3-triazole linked galactopyranosides and evaluation of cholera toxin inhibition

Pyridoxine-derived bicyclic aminopyridinol antioxidants: synthesis and their antioxidant activities

Multi-component, regio-selective aldol addition of β-ketoesters to aldehydes: scope and applications

C₃-triiodocyclotriveratrylene as a key intermediate to fluorescent probes: application to selective choline recognition

Improvement of in vitro-transcribed amber suppressor tRNAs toward higher suppression efficiency in wheat germ extract

Additions and corrections published in 2011

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Pyridinium/urea-based anion receptor: methine formation in the presence of basic anions

Content Provider	Royal Society of Chemistry (RSC)
Author	Bergamaschi, Greta Amendola, Valeria Boiocchi, Massimo Monzani, Enrico
Copyright Year	2011
Abstract	The influence of the positively charged N-methylpyridinium substituent on the anion binding tendencies of urea-based receptors has been investigated by comparing molecules 1 and 2. These receptors have been studied in acetonitrile, by performing UV-vis. and 1H NMR titrations with several anions. UV-vis. titrations have also been performed in DMSO, MeOH and CHCl3/CH3CN mixture (1/1, v/v). In the case of 1, the presence of both H-donor and H-acceptor groups (urea and pyridine, respectively) favours aggregation and the formation of dimers in the solid state. In solution, this tendency to aggregate reduces affinity for anions with respect to the similar urea-based receptor 3. The methylation of the pyridyl group of 1 leads to the pyridinium-containing receptor 2. The pyridinium positive charge enhances the acidity of urea and increases anion affinity, as evidenced by the comparison of the binding constants. Both receptors (1–2) form stable adducts with all investigated anions. However, in the case of 2, the formation of 1 : 1 adducts with basic anions, such as acetate and fluoride, is followed by a proton transfer process. Quite interestingly, deprotonation does not involve the urea group, thus preserving the 1 : 1 adduct, as demonstrated by the 1H NMR measurements. In particular, the proton transfer process takes place at the methylene group linking the pyridinium fragment to the receptor's skeleton. 1H NMR studies indicate the formation of a stable neutral methine species, characterised by the loss of aromaticity by the pyridyl ring. These results open new perspectives in the field of anion recognition, as receptor 2 may by applied to the monitoring of both bound anion (through the urea unit) and excess anion in solution (through the development of the yellow methine species).
Starting Page	8276
Ending Page	8283
Page Count	8
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	9
Issue Number	24
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c1ob06193c
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Estrogen receptor Aromaticity DMSO Fluorine Pyridinium Ion Nuclear magnetic resonance spectroscopy Methine group Substituent Methylene group Urea Pyridine Acetonitrile Dimethyl sulfoxide Proton Methylation Adduct
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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Positive and negative allosteric effects of thiacalix[4]arene-based receptors having urea and crown-ether moieties

Complex interactions of pillar[5]arene with paraquats and bis(pyridinium) derivatives

Fluorescent carbazolylurea anion receptors

Synthesis, characterization, photophysics, and anion binding properties of platinum(II) acetylide complexes with urea group

The crystallisation of polyoxo-molybdate and -tungstate anions with phenylated phosphonium and arsonium cations, in relation to the crystal packing and species in solution

Aggregation of amphiphilic compounds in dimethyl sulfoxide: example of non-ionic alkyl–fluoroalkyl lipopeptides

Equilibrium acidities of BINOL type chiral phenolic hydrogen bonding donors in DMSO

Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolines

Synthesis and NMR and mass spectrometric study of ammonioacetohydrazones of formylphenylboronic acids as novel ionic prospective sugar receptors

Pyridinium/urea-based anion receptor: methine formation in the presence of basic anions

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