U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H24O6
Molecular Weight 264.3154
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 18-CROWN-6

SMILES

C1COCCOCCOCCOCCOCCO1

InChI

InChIKey=XEZNGIUYQVAUSS-UHFFFAOYSA-N
InChI=1S/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
Preparation and structural characterisation of methoxybis(trimethylsilyl)silyl potassium and its condensation product.
2004-08-07
The development of a continuous isothermal titration calorimetric method for equilibrium studies.
2004-08-01
Possible role of relativistic effects in the plasticity of the coordination geometry of cadmium(II). A voltammetric study of the stability of the complexes of cadmium(II) with 12-crown-4,15-crown-5 and 18-crown-6 in aqueous solution and the structures of [Cd(benzo-18-crown-6)(NCS)(2)] and [K(18-crown-6)][Cd(SCN)(3)].
2004-07-12
Calorimetric vs. van't Hoff binding enthalpies from isothermal titration calorimetry: Ba2+-crown ether complexation.
2004-07-01
Synthesis of double-armed lariat ethers with pyrene moieties at each end of two sidearms and their fluorescence properties in the presence of alkali metal and alkaline earth metal cations.
2004-06-25
Simultaneous determination of catecholamines and polyamines in PC-12 cell extracts by micellar electrokinetic capillary chromatography with ultraviolet absorbance detection.
2004-06-15
Distorted equatorial coordination environments and weakening of U=O bonds in uranyl complexes containing NCN and NPN ligands.
2004-05-17
Spacer length effect of a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid.
2004-05-15
Crystallographic distinction between "contact" and "separated" ion pairs: structural effects on electronic/ESR spectra of alkali-metal nitrobenzenides.
2004-04-14
Chiral discrimination studies of (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid by high-performance liquid chromatography and NMR spectroscopy.
2004-04
Two complexes of Sm(II) with crown ethers-electrochemical synthesis, structure and spectroscopy.
2004-03-07
Protonated nucleobase ligands: synthesis, structure and characterization of 9-methyladeninium hexachloroplatinate and pentachloro(9-methyladeninium)platinum(IV).
2004-03
Nucleophilic displacement on 4-nitrophenyl dimethyl phosphinate by ethoxide ion: alkali metal ion catalysis and mechanism.
2004-02-21
Ion chromatographic separation of hydrogen ion and other common mono- and divalent cations.
2004-01-16
Biological activity of bacterial lectins and their molecular complexes with heterocyclic bis-adducts.
2004-01-16
Ethylenediamine as a liquid chemical reagent to probe hydrogen bonding and host-guest interactions with crown ethers in an ion trap tandem mass spectrometer.
2004
Crystal and molecular structures of ionophore-siderophore host-guest supramolecular assemblies relevant to molecular recognition.
2003-12-03
CE/electrospray ionization-MS analysis of underivatized d/l-amino acids and several small neurotransmitters at attomole levels through the use of 18-crown-6-tetracarboxylic acid as a complexation reagent/background electrolyte.
2003-11-15
Isolation, characterization, and reaction of activated iodosylbenzene monomer hydroxy(phenyl)iodonium ion with hypervalent bonding: supramolecular complex PhI+OH.18-crown-6 with secondary I...O interactions.
2003-10-29
Use of mobile phase 18-crown-6 to improve peak resolution between mono- and divalent metal and amine cations in ion chromatography.
2003-10-24
H+, Na+ and K+ modulated lanthanide luminescent switching of Tb(III) based cyclen aromatic diaza-crown ether conjugates in water.
2003-10-07
Computational assessment of the electronic structure of 1-azacyclohexa-2,3,5-triene (3 delta 2-1H-pyridine) and its benzo derivative (3 delta 2-1H-quinoline) as well as generation and interception of 1-methyl-3 delta 2-1H-quinoline.
2003-10-06
The isothiocyanate complex of triphenylborane forms an unusual coordination polymer with [K(18-crown-6)](+), both in the solid state and in solution.
2003-10
Chemical activation of cytochrome c proteins via crown ether complexation: cold-active synzymes for enantiomer-selective sulfoxide oxidation in methanol.
2003-09-24
Sonogashira coupling using bulky palladium-phenanthryl imidazolium carbene catalysis.
2003-09-04
From 1D strands to extended molecular assemblies in the binary compounds of dithiooxamide and dithiobiurea with crown ethers.
2003-08-21
Enantiomeric separation of TAPP, H-Tyr-(D)Ala-Phe-Phe-NH(2), by capillary electrophoresis using 18-crown-6-tetracarboxylic acid as a chiral selector.
2003-08-15
Synthesis of a new potential tridentate anthracene ligand bearing deprotectable methoxymethoxy (OMOM) group at 1,8-positions: attempt to synthesize anionic hypervalent carbon compounds.
2003-08-04
Photonic crystal optrode sensor for detection of Pb2+ in high ionic strength environments.
2003-08-01
Potassium dicyanoargentate(I) 1,4,7,10,13,16-hexaoxacyclooctadecane.
2003-08
Controlling the conformation and interplay of p-sulfonatocalix[6]arene as lanthanide crown ether complexes.
2003-06-16
High-speed simultaneous ion-exclusion/cation-exchange chromatography of anions and cations on a weakly acidic cation-exchange resin column.
2003-05-16
Synthesis, characterization, and reaction of ethynyl(phenyl)-lambda3-iodane complex with [18]crown-6.
2003-05-16
A theoretical study of the large Hg-Hg spin-spin coupling constants in Hg(2)(2+), Hg(3)(2+), and Hg(2)(2+)-crown ether complexes.
2003-04-23
Single complexation force of 18-crown-6 with ammonium ion evaluated by atomic force microscopy.
2003-04-16
Electron transfer between two silyl-substituted phenylene rings: EPR/ENDOR spectra, DFT calculations, and crystal structure of the one-electron reduction compound of a di(m-silylphenylenedisiloxane).
2003-04-16
An equilibrium partitioning model for predicting response to host-guest complexation in electrospray ionization mass spectrometry.
2003-04-15
Evaluation of diabetic ketoacidosis-related ionic metabolites in human blood serum by capillary electrophoresis.
2003-04
Threshold dissociation energies of protonated amine/polyether complexes in a quadrupole ion trap.
2003-04
Near infrared spectral investigations of hydration of 18-crown-6 in HDO-D2O solutions at different temperatures.
2003-04
Secondary hypervalent I(III)...O interactions: synthesis and structure of hypervalent complexes of diphenyl-lambda3-iodanes with 18-crown-6.
2003-01-22
Preparation and application of a new modified liquid chromatographic chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid.
2003-01-17
Enantioselective ion-exclusion chromatography on teicoplanin aglycone and (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid stationary phases.
2003-01-03
Crown ethers as ancillary ligands in the assembly of silver(i) aggregates containing embedded acetylenediide.
2003-01-03
Probing the discriminating power of chiral crown hosts by CD spectroscopy.
2003
Effect of acidity on the enantiomeric resolution of thyroxine and tocainide by HPLC on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid column.
2002-12-31
From one-dimensional chain to pentanuclear molecule. Magnetism of cyano-bridged Fe(III)-Ni(II) complexes.
2002-12-16
Structural and vibrational study of the Ci(1) conformation of 18-crown-6.
2002-11
Simultaneous determination of inorganic and organic anions, alkali, alkaline earth and transition metal cations by capillary electrophoresis with contactless conductometric detection.
2002-11
A unique spherical molecular host with D2d symmetry. A novel intramolecular kinetic equilibrium in metal ion complexation between two crown ethers.
2002-10-31
Patents
Name Type Language
18-CROWN-6
Common Name English
NSC-159836
Preferred Name English
18-CROWN ETHER-6
Common Name English
1,4,7,10,13,16-HEXAOXACYCLOOCTADECANE
Systematic Name English
ETHYLENE OXIDE CYCLIC HEXAMER
Common Name English
Code System Code Type Description
CHEBI
32397
Created by admin on Mon Mar 31 18:57:01 GMT 2025 , Edited by admin on Mon Mar 31 18:57:01 GMT 2025
PRIMARY
MESH
C015762
Created by admin on Mon Mar 31 18:57:01 GMT 2025 , Edited by admin on Mon Mar 31 18:57:01 GMT 2025
PRIMARY
EPA CompTox
DTXSID7058626
Created by admin on Mon Mar 31 18:57:01 GMT 2025 , Edited by admin on Mon Mar 31 18:57:01 GMT 2025
PRIMARY
FDA UNII
63J177NC5B
Created by admin on Mon Mar 31 18:57:01 GMT 2025 , Edited by admin on Mon Mar 31 18:57:01 GMT 2025
PRIMARY
ECHA (EC/EINECS)
241-473-5
Created by admin on Mon Mar 31 18:57:01 GMT 2025 , Edited by admin on Mon Mar 31 18:57:01 GMT 2025
PRIMARY
CAS
17455-13-9
Created by admin on Mon Mar 31 18:57:01 GMT 2025 , Edited by admin on Mon Mar 31 18:57:01 GMT 2025
PRIMARY
NSC
159836
Created by admin on Mon Mar 31 18:57:01 GMT 2025 , Edited by admin on Mon Mar 31 18:57:01 GMT 2025
PRIMARY
PUBCHEM
28557
Created by admin on Mon Mar 31 18:57:01 GMT 2025 , Edited by admin on Mon Mar 31 18:57:01 GMT 2025
PRIMARY
WIKIPEDIA
18-CROWN-6
Created by admin on Mon Mar 31 18:57:01 GMT 2025 , Edited by admin on Mon Mar 31 18:57:01 GMT 2025
PRIMARY