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[1]
Identifiers
33100-27-5 YesY
1618144
ChEBI CHEBI:32401 YesY
ChEMBL ChEMBL156289 YesY
ChemSpider 33416 YesY
EC Number 251-379-6
3897
Jmol 3D model Interactive image
MeSH 15-Crown-5
PubChem 36336
RTECS number SB0200000
  • InChI=1S/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2 YesY
    Key: VFTFKUDGYRBSAL-UHFFFAOYSA-N YesY
  • InChI=1/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2
    Key: VFTFKUDGYRBSAL-UHFFFAOYAH
  • C1COCCOCCOCCOCCO1
Properties
C10H20O5
Molar mass 220.27 g·mol−1
Appearance Clear, colorless liquid
Density 1.113 g cm−3 (at 20 °C)
Boiling point 93–96 °C (199–205 °F; 366–369 K) at 0.05 mmHg
log P -0.639
1.465
Thermochemistry
-881.1--877.1 kJ mol−1
-5.9157--5.9129 MJ mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

15-Crown-5 is a crown ether with the formula (C2H4O)5. It is a cyclic pentamer of ethylene oxide that forms complex with various cations, including sodium (Na+)[2] and potassium (K+),[3] however, it is complementary to Na+ and thus has a higher selectivity for Na+ ions.

Properties

Analogous to 18-crown-6, 15-crown-5 binds to sodium ions. Thus, when treated with this complexing agent, sodium salts often become soluble in organic solvents.

First-row transition metal dications fit snugly inside the cavity of 15-crown-5. They are too small to be included in 18-crown-6. The binding of transition metal cations results in multiple hydrogen-bonded interactions from both equatorial and axial aqua ligands, such that highly crystalline solid-state supramolecular polymers can be isolated. Metal salts isolated in this form include Co(ClO4)2, Ni(ClO4)2, Cu(ClO4)2, and Zn(ClO4)2. Seven coordinate species are most common for transition metal ions complexes of 15-crown-5, with the crown ether occupying the equatorial plane, along with 2 axial aqua ligands.[4]

File:Cobalt complex with 15-crown-5.png
The structure of the complex [Co(15-crown-5)(H2O)2]2+.

15-crown-5 have also been used to isolate salts of oxonium ions. For example, from a solution of tetrachloroauric acid, the oxonium ion [H7O3]+ has been isolated as the salt [(H7O3)(15-crown-5)2][AuCl4]. Neutron diffraction studies revealed a sandwich structure, which shows a chain of water with remarkably long O-H bond (1.12 Å) in the acidic proton, but with a very short OH•••O distance (1.32 Å).[4]

File:((H7O3)(15-crown-5))+.jpg
Structure of [(H7O3)(15-crown-5)2]+ ion

A derivative of 15-crown-5, benzo-15-crown-5, has been used to produce anionic complexes of carbido ligands as their [K(benzo-15-crown-5)2]+ salts:[4]

(Ar2N)3MoCH + KCH2Ph + 2 15-crown-5 → [K(15-crown-5)2]+[(Ar2N)3MoC]− + CH3Ph

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ 4.0 4.1 4.2 Lua error in package.lua at line 80: module 'strict' not found.

Further reading

  • Lua error in package.lua at line 80: module 'strict' not found.
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External links

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