Dibenzo-18-crown-6

Dibenzo-18-crown-6
Identifiers
CAS Number	14187-32-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:358732 ;
ChEMBL	ChEMBL345536 ;
ChemSpider	24722 ;
ECHA InfoCard	100.034.568
KEGG	C14289 ;
PubChem CID	26541;
UNII	0A7W45JCS9 ;
CompTox Dashboard (EPA)	DTXSID6022428 ;
	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 Key: YSSSPARMOAYJTE-UHFFFAOYSA-N ; 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;
	SMILES 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

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

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.
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.

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[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.