9-Crown-3

9-Crown-3
Names
	Preferred IUPAC name 1,4,7-Trioxonane
	Other names 1,4,7-Trioxacyclononane; Ethylene oxide trimer
Identifiers
CAS Number	27725-91-3;
3D model (JSmol)	Interactive image;
Beilstein Reference	1421638
ChEBI	CHEBI:32400;
ChemSpider	480221;
PubChem CID	552016;
CompTox Dashboard (EPA)	DTXSID70338923 ;
	InChI InChI=1S/C6H12O3/c1-2-8-5-6-9-4-3-7-1/h1-6H2 Key: RCIDBLLMZGGECJ-UHFFFAOYSA-N;
	SMILES C1COCCOCCO1;
Properties
Chemical formula	C6H12O3
Molar mass	132.159 g·mol−1
Appearance	colorless liquid
Melting point	0 °C (32 °F; 273 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

9-Crown-3, also called 1,4,7-trioxonane or 1,4,7-trioxacyclononane is a crown ether with the formula (C₂H₄O)₃. A colorless liquid, it is obtained in low yield by the acid-catalyzed oligomerization of ethylene oxide.^[1]

In contrast to larger crown ethers (12-crown-4, and 18-crown-6), 9-crown-3 has elicited very little interest, except from theorists.^[2]^[3]

References

^ Dale, Johannes; Borgen, Gerd; Daasvatn, Kari; Liaaen-Jensen, Synnøve; Enzell, Curt R.; Mannervik, Bengt (1974). "The Oligomerization of Ethylene Oxide to Macrocyclic Ethers, Including 1,4,7-Trioxacyclononane". Acta Chemica Scandinavica. 28b: 378–379. doi:10.3891/acta.chem.scand.28b-0378.
^ Anderson, Wayne P.; Behm, Philip; Glennon, Timothy M.; Zerner, Michael C. (1997-03-01). "Quantum Mechanics and Molecular Mechanics Studies of the Low-Energy Conformations of 9-Crown-3". The Journal of Physical Chemistry A. 101 (10): 1920–1926. Bibcode:1997JPCA..101.1920A. doi:10.1021/jp962172h. ISSN 1089-5639.
^ Jagannadh, B.; Sarma, Jagarlapudi A. R. P. (1999-12-01). "Searching the Conformational Space of Cyclic Molecules: A Molecular Mechanics and Density Functional Theory Study of 9-Crown-3". The Journal of Physical Chemistry A. 103 (50): 10993–10997. Bibcode:1999JPCA..10310993J. doi:10.1021/jp991201w. ISSN 1089-5639.

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[1] Dale, Johannes; Borgen, Gerd; Daasvatn, Kari; Liaaen-Jensen, Synnøve; Enzell, Curt R.; Mannervik, Bengt (1974). "The Oligomerization of Ethylene Oxide to Macrocyclic Ethers, Including 1,4,7-Trioxacyclononane". Acta Chemica Scandinavica. 28b: 378–379. doi:10.3891/acta.chem.scand.28b-0378.

[2] Anderson, Wayne P.; Behm, Philip; Glennon, Timothy M.; Zerner, Michael C. (1997-03-01). "Quantum Mechanics and Molecular Mechanics Studies of the Low-Energy Conformations of 9-Crown-3". The Journal of Physical Chemistry A. 101 (10): 1920–1926. Bibcode:1997JPCA..101.1920A. doi:10.1021/jp962172h. ISSN 1089-5639.

[3] Jagannadh, B.; Sarma, Jagarlapudi A. R. P. (1999-12-01). "Searching the Conformational Space of Cyclic Molecules: A Molecular Mechanics and Density Functional Theory Study of 9-Crown-3". The Journal of Physical Chemistry A. 103 (50): 10993–10997. Bibcode:1999JPCA..10310993J. doi:10.1021/jp991201w. ISSN 1089-5639.

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See also

References