Browse
Submit Data
Databases
API
Help

Dataset Information

30 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A quinoline based bis-urea receptor for anions: a selective receptor for hydrogen sulfate.

ABSTRACT: A dipodal bis-urea receptor has been synthesized from the reaction of 8-amino quinoline and 1,4-phenylene diisocyanate in dichloromethane, and the anion binding ability of the receptor has been studied using fluoride, chloride, bromide, iodide, perchlorate, nitrate, dihydrogen phosphate and hydrogen sulfate by UV-Vis titrations in DMSO. The results show that the receptor binds each of the anions with a 1:1 stoichiometry, showing high affinity and moderate selectivity for hydrogen sulfate among the anions studied. Ab initio calculations based on density functional theory (DFT) suggest that an anion (X(-)) is bonded within the cleft formed by the two arms of the receptor through two NH...X(-) and two aromatic CH...X(-) interactions. The results from solution and theoretical studies suggest that binding is predominantly influenced by hydrogen bonding interactions and the basicity of anions.

SUBMITTER: Russ TH

PROVIDER: S-EPMC3342016 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

A quinoline based bis-urea receptor for anions: a selective receptor for hydrogen sulfate.

Russ Tiffany H TH Pramanik Avijit A Khansari Maryam E ME Wong Bryan M BM Hossain Md Alamgir MA

Natural product communications 20120301 3

A dipodal bis-urea receptor has been synthesized from the reaction of 8-amino quinoline and 1,4-phenylene diisocyanate in dichloromethane, and the anion binding ability of the receptor has been studied using fluoride, chloride, bromide, iodide, perchlorate, nitrate, dihydrogen phosphate and hydrogen sulfate by UV-Vis titrations in DMSO. The results show that the receptor binds each of the anions with a 1:1 stoichiometry, showing high affinity and moderate selectivity for hydrogen sulfate among t ...[more]

PMID: 22545400

Similar Datasets

(R,R)-Disynephrine ether bis-(hydrogen sulfate).

Project description:THE ASYMMETRIC UNIT OF THE TITLE COMPOUND [SYSTEMATIC NAME: (R,R)-2,4-bis-(4-hydroxy-phen-yl)-N,N'-dimethyl-3-oxapentane-1,5-diammonium bis-(hydrogen sulfate)], C(18)H(26)N(2)O(3) (2+)·2HSO(4) (-), contains one half-cation and one hydrogen sulfate anion. The cation has crystallographically imposed twofold symmetry with the rotation axis passing through the central ether O atom. Hydrogen bonds between the hydr-oxy group and amine H atoms of the cation to two hydrogen sulfate anions link the three ions in a ring motif. A three-dimensional network is accomplished by additional O-H?O hydrogen bonds between the anions and by N-H?O hydrogen bonds between the cations. Disorder with equally occupied sites affects the H-atom position in the anion.

| S-EPMC2977255 | biostudies-literature

1-Phenyl-piperazine-1,4-diium bis-(hydrogen sulfate).

Project description:In the title compound, C(10)H(16)N(2) (2+)·2HSO(4) (-), the S atoms adopt slightly distorted tetra-hedral geometry and the diprotonated piperazine ring adopts a chair conformation. In the crystal, the 1-phenyl-piperazine-1,4-diium cations are anchored between chains formed by the sulfate entities via inter-molecular bifurcated N-H?(O,O) and weak C-H?O hydrogen bonds. These hydrogen bonds contribute to the cohesion and stability of the network of the crystal structure.

| S-EPMC2983403 | biostudies-literature

Crystal structure of 1,3-bis-(1,3-dioxoisoindolin-1-yl)urea dihydrate: a urea-based anion receptor.

Project description:The whole mol-ecule of the title compound, C17H10N4O5·2H2O, is generated by twofold rotation symmetry and it crystallized as a dihydrate. The planes of the phthalimide moieties and the urea unit are almost normal to one another, with a dihedral angle of 78.62?(9)°. In the crystal, mol-ecules are linked by N-H?O and O-H?O hydrogen bonds, forming a three-dimensional framework structure. The crystal packing also features C-H?O hydrogen bonds and slipped parallel ?-? inter-actions [centroid-centroid distance = 3.6746?(15)?Å] involving the benzene rings of neighbouring phthalimide moieties.

| S-EPMC4257348 | biostudies-literature

Crystal structure of a host-guest complex of the tris-urea receptor, 3-(4-nitro-phen-yl)-1,1-bis-{2-[3-(4-nitro-phen-yl)ureido]eth-yl}urea, that encapsulates hydrogen-bonded chains of di-hydrogen phosphate anions with separate tetra-<i>n</i>-butyl-ammonium counter-ions.

Project description:The title compound, C25H25N9O9·C16H36N+·H2PO4 - (I) or (C25H25N9O9)·(n-Bu4N+)·(H2PO4 -) (systematic name: 3-(4-nitro-phen-yl)-1,1-bis-{2-[3-(4-nitro-phen-yl)ureido]eth-yl}urea tetra-butyl-ammonium di-hydrogen phosphate), comprises a tris-urea receptor (R), a di-hydrogen phosphate anion and a tetra-n-butyl-ammonium cation. It crystallizes with two independent formula units in the asymmetric unit. The conformations of the two tris-urea receptors are stabilized by N-H⋯O and C-H⋯O intra-molecular hydrogen bonds. Each di-hydrogen phosphate anion has two O-H⋯O inter-molecular hydrogen-bonding inter-actions with the other di-hydrogen phosphate anion. Inversion-related di-anion units are linked by further O-H⋯O hydrogen bonds, forming a chain propagating along the a-axis direction. Each di-hydrogen phosphate anion makes a total of four N-H⋯O(H2PO4 -) hydrogen bonds with two ureido subunits from two different tris-urea receptors, hence each tris-urea receptor provides the two ureido subunits for the encapsulation of the H2PO4 - hydrogen-bonded chain. There are numerous inter-molecular C-H⋯O hydrogen bonds present involving both receptor mol-ecules and the tetra-n-butyl-ammonium cations, so forming a supra-molecular three-dimensional structure. One of the butyl groups and one of the nitro groups are disordered over two positions of equal occupancy.

| S-EPMC6399704 | biostudies-literature

Seven-coordinate anion complex with a tren-based urea: binding discrepancy of hydrogen sulfate in solid and solution states.

Project description:Structural characterization of a hydrogen sulfate complex with a tren-based urea suggests that the anion is coordinated with six NH···O bonds (d(N···O) = 2.857 (3) to 3.092 (3) Å) and one OH···O bond (d(O···O) = 2.57 (2) Å) from three receptors; however, in solution the anion is bound within the pseudo-cavity of one receptor.

| S-EPMC3306551 | biostudies-literature

Synthesis and anion binding studies of tris(3-aminopropyl)amine-based tripodal urea and thiourea receptors: Proton transfer-induced selectivity for hydrogen sulfate over sulfate.

Project description:Tris(3-aminopropyl)amine-based tripodal urea and thiourea receptors, tris([(4-cyanophenyl)amino]propyl)urea (L1) and tris([(4-cyanophenyl)amino]propyl)thiourea (L2), have been synthesized and their anion binding properties have been investigated for halides and oxoanions. As investigated by 1H NMR titrations, each receptor binds an anion with a 1:1 stoichiometry via hydrogen-bonding interactions (NH⋯anion), showing the binding trend in the order of F- > H2PO4- > HCO3- > HSO4- > CH3COO- > SO42- > Cl- > Br- > I in DMSO-d6 . The interactions of the receptors were further studied by 2D NOESY, showing the loss of NOESY contacts of two NH resonances for the complexes of F-, H2PO4-, HCO3-, HSO4- or CH3COO- due to the strong NH⋯anion interactions. The observed higher binding affinity for HSO4- than SO42- is attributed to the proton transfer from HSO4- to the central nitrogen of L1 or L2 which was also supported by the DFT calculations, leading to the secondary acid-base interactions. The thiourea receptor L2 has a general trend to show a higher affinity for an anion as compared to the urea receptor L1 for the corresponding anion in DMSO-d6 . In addition, the compound L2 has been exploited for its extraction properties for fluoride in water using a liquid-liquid extraction technique, and the results indicate that the receptor effectively extracts fluoride from water showing ca. 99% efficiency (based on L2).

| S-EPMC5295472 | biostudies-literature

A bis-chalcone based colorimetric probe for the selective detection of bisulfite/sulfite anions: exploring surfactant promoted Michael addition of anions to α, β-unsaturated ketones.

Project description:A probe, (1E,4E)-1,5-di(thiophen-2-yl)penta-1,4-dien-3-one, was developed for rapid, colorimetric, and selective detection of bisulfite/sulfite anions in aqueous solutions. This probe is based on the Michael addition reaction which is favoured in the presence of cationic micellar medium CTAB. CTAB promoted Michael addition is an effective tool to determine SO2 toxicity, which is mainly expressed in terms of collective concentration of bisulfite and sulfite anions. The probe showed high selectivity and sensitivity toward bisulfite and sulfite over other interfering anions, with a detection limit of 0.43 μM and 0.23 μM, respectively. The possible recognition mechanism of the probe and the analyte was illustrated by NMR, HR-MS, IR, and computational analysis. Moreover, this probe showed great potential for the detection of bisulfite/sulfite in real samples, such as crystal sugar and brown sugar.

| S-EPMC9843694 | biostudies-literature

Bis-aryl urea derivatives as potent and selective LIM kinase (Limk) inhibitors.

Project description:The discovery/optimization of bis-aryl ureas as Limk inhibitors to obtain high potency and selectivity and appropriate pharmacokinetic properties through systematic SAR studies is reported. Docking studies supported the observed SAR. Optimized Limk inhibitors had high biochemical potency (IC50 < 25 nM), excellent selectivity against ROCK and JNK kinases (>400-fold), potent inhibition of cofilin phosphorylation in A7r5, PC-3, and CEM-SS T cells (IC50 < 1 ?M), and good in vitro and in vivo pharmacokinetic properties. In the profiling against a panel of 61 kinases, compound 18b at 1 ?M inhibited only Limk1 and STK16 with ?80% inhibition. Compounds 18b and 18f were highly efficient in inhibiting cell-invasion/migration in PC-3 cells. In addition, compound 18w was demonstrated to be effective on reducing intraocular pressure (IOP) on rat eyes. Taken together, these data demonstrated that we had developed a novel class of bis-aryl urea derived potent and selective Limk inhibitors.

| S-EPMC4349585 | biostudies-literature

Near Quantitative Removal of Selenate and Sulfate Anions from Wastewaters by Cocrystallization with Chelating Hydrogen-Bonding Guanidinium Ligands.

Project description:Selenium (Se) has become an environmental contaminant of aquatic ecosystems as a result of human activities, particularly mining, fossil fuel combustion, and agricultural activities. By leveraging the high sulfate concentrations relative to Se oxyanions (i.e., SeO n 2-, n = 3, 4) present in some wastewaters, we have developed an efficient approach to Se-oxyanion removal by cocrystallization with bisiminoguanidinium (BIG) ligands that form crystalline sulfate/selenate solid solutions. The crystallization of the sulfate, selenate and selenite, oxyanions and of sulfate/selenate mixtures with five candidate BIG ligands are reported along with the thermodynamics of crystallization and aqueous solubilities. Oxyanion removal experiments with the top two performing candidate ligands show a near quantitative removal (>99%) of sulfate or selenate from solution. When both sulfate and selenate are present, there is near quantitative removal (>99%) of selenate, down to sub-ppb Se levels, with no discrimination between the two oxyanions during cocrystallization. Reducing the selenate concentrations by 3 orders of magnitude or more relative to sulfate, as found in many wastewaters, led to no measurable loss in Se removal efficiencies. This work offers a simple and effective alternative to selective separation of trace amounts of highly toxic selenate oxyanions from wastewaters, to meet stringent regulatory discharge limits.

| S-EPMC10052226 | biostudies-literature

Crystal structure of the 1:2 adduct of bis-(piperidinium) sulfate and 1,3-di-methyl-thio-urea.

Project description:In the title compound, 2C5H12N+·SO42-·2C3H8N2S, the C=S groups of the two independent 1,3-di-methyl-urea mol-ecules and the sulfur atom of the anion lie on twofold axes. The packing is centred on bis-(piperidinium) sulfate ribbons parallel to the c axis; the cations are hydrogen bonded to the sulfate by N-H⋯O and C-H⋯O inter-actions. The 1,3-di-methyl-urea mol-ecules are also hydrogen bonded to sulfate O atoms, and project outwards from the ribbon parallel to the b axis.

| S-EPMC5418776 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data