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15-Crown-5

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15-Crown-5
Skeletal formula
Ball-and-stick model
Names
Systematic IUPAC name 1,4,7,10,13-Pentaoxacyclopentadecane
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1618144
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.046.694 Edit this at Wikidata
EC Number
  • 251-379-6
Gmelin Reference 3897
MeSH 15-Crown-5
PubChem CID
RTECS number
  • SB0200000
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2Key: VFTFKUDGYRBSAL-UHFFFAOYSA-N
  • InChI=1/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2Key: VFTFKUDGYRBSAL-UHFFFAOYAH
SMILES
  • C1COCCOCCOCCOCCO1
Properties
Chemical formula C10H20O5
Molar mass 220.265 g·mol
Appearance Transparent liquid
Density 1.113 g cm (at 20 °C)
Boiling point 116 °C (241 °F; 389 K)
log P -0.639
Refractive index (nD) 1.465
Thermochemistry
Std enthalpy of
formation
fH298)
-881.1--877.1 kJ mol
Std enthalpy of
combustion
cH298)
-5.9157--5.9129 MJ mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H315, H319
Precautionary statements P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 1 0
Flash point 113 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

15-Crown-5 is a crown ether with the formula C10H20O5. It is a cyclic pentamer of ethylene oxide that has been shown to complex with various cations, including sodium (Na) and potassium (K), but selective binding to lead (Pb).

As a functional group, research has been conducted to probe its application in liquid crystalline studies, ion-selective membranes, chromo- and fluoroionophores.

See also

References

  1. "15-crown-5 - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 11 October 2011.
  2. Takeda, Y.; et al. (1998). "A Conductance Study of 1:1 Complexes of 15-Crown-5, 16-Crown-5, and Benzo-15-crown-5 with Alkali Metal Ions in Nonaqueous Solvents". Bulletin of the Chemical Society of Japan. 61 (3): 627–632. {{cite journal}}: Explicit use of et al. in: |author= (help)
  3. Chen, Chun-Yen; et al. (2006). "Potassium ion recognition by 15-crown-5 functionalized CdSe/ZnS quantum dots in H2O". Chem. Comm. (3): 263–265. doi:10.1039/B512677K. {{cite journal}}: Explicit use of et al. in: |author= (help)
  4. "Mesogenic Properties of 15-Crown-5-Ether - Derivatives" (PDF). Retrieved 2008-11-19.
  5. Klok, H.A.; et al. (1997). "Novel benzo-15-crown-5 functionalized α-olefin/CO terpolymers for membrane applications". Macromolecular Chemistry and Physics. 198 (9): 2759–2768. doi:10.1002/macp.1997.021980908. {{cite journal}}: Explicit use of et al. in: |author= (help)
  6. Fedorova, O.A.; et al. (2005). "Facile synthesis of novel styryl ligands containing a 15-crown-5 ether moiety". Arkivoc. xv: 12–24. {{cite journal}}: Explicit use of et al. in: |author= (help)

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