Dibenzo-18-crown-6

Dibenzo-18-crown-6
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
6,7,9,10,17,18,20,21-Octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecine
Identifiers
CAS Number
  • 14187-32-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:358732 checkY
ChEMBL
  • ChEMBL345536 checkY
ChemSpider
  • 24722 checkY
ECHA InfoCard 100.034.568 Edit this at Wikidata
KEGG
  • C14289 checkY
PubChem CID
  • 26541
UNII
  • 0A7W45JCS9 checkY
CompTox Dashboard (EPA)
  • DTXSID6022428 Edit this at Wikidata
InChI
  • InChI=1S/C20H24O6/c1-2-6-18-17(5-1)23-13-9-21-11-15-25-19-7-3-4-8-20(19)26-16-12-22-10-14-24-18/h1-8H,9-16H2 checkY
    Key: YSSSPARMOAYJTE-UHFFFAOYSA-N checkY
  • InChI=1/C20H24O6/c1-2-6-18-17(5-1)23-13-9-21-11-15-25-19-7-3-4-8-20(19)26-16-12-22-10-14-24-18/h1-8H,9-16H2
    Key: YSSSPARMOAYJTE-UHFFFAOYAB
  • O1c3c(OCCOCCOc2ccccc2OCCOCC1)cccc3
Properties
Chemical formula
 C20H24O6
Molar mass 360.406 g·mol−1
Appearance white solid
Melting point 162.5–163.5 °C (324.5–326.3 °F; 435.6–436.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

Dibenzo-18-crown-6 is the organic compound with the formula [OC6H4OCH2CH2OCH2CH2]2. It is a white solid that is soluble in organic solvents. As one of the most popular crown ethers, it facilitates the dissolution of many salts in organic solvents. It is related to the non-benzannulated 18-crown-6.

Dibenzo-18-crown-6 can be synthesized from catechol and bis(chloroethyl) ether.[1]

In contrast to those of 18-crown-6, complexes of the dibenzo crown are flattened, which often allows higher coordination numbers at the encapsulated metal cation.

Structure of [Na(dibenzo-18-c-6)]+, as found in the FeCl4− salt.[2]

References

  1. ^ Charles J. Pedersen (1972). "Macrocyclic Polyethers: Dibenzo-18-Crown-6 Polyether and Dicyclohexyl-18-Crown-6 Polyether". Organic Syntheses. 52: 66. doi:10.15227/orgsyn.052.0066.
  2. ^ Rogers, Robin D.; Song, Ying (1995). "The crystal structure of a heterobimetallic crown ether complex: [Na(dibenzo-18-crown-6)][FeCl4]". Journal of Chemical Crystallography. 25 (9): 579–582. doi:10.1007/BF01667027. S2CID 93955378.