1,4,7,10,13,16-Hexaoxacyclooctadecane

• Formula: C₁₂H₂₄O₆
• Molecular weight: 264.3154
• IUPAC Standard InChI: InChI=1S/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2 Copy

  
• IUPAC Standard InChIKey: XEZNGIUYQVAUSS-UHFFFAOYSA-N Copy
• CAS Registry Number: 17455-13-9
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Ethylene oxide cyclic hexamer; 18-Crown-6; 18-Crown-6 ether; Crown ether 18-crown-6
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
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Condensed phase thermochemistry data

Go To: Top, Reaction thermochemistry data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Reaction thermochemistry data

Go To: Top, Condensed phase thermochemistry data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₄H₅N₂⁺ +  = (C₄H₅N₂⁺ • )

By formula: C₄H₅N₂⁺ + C₁₂H₂₄O₆ = (C₄H₅N₂⁺ • C₁₂H₂₄O₆)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Free energy of reaction

C₅H₆N⁺ +  = (C₅H₆N⁺ • )

By formula: C₅H₆N⁺ + C₁₂H₂₄O₆ = (C₅H₆N⁺ • C₁₂H₂₄O₆)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Free energy of reaction

C₆H₁₄N⁺ +  = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₁₂H₂₄O₆ = (C₆H₁₄N⁺ • C₁₂H₂₄O₆)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Free energy of reaction

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₁₂H₂₄O₆ = (C₃H₁₀N⁺ • C₁₂H₂₄O₆)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Free energy of reaction

 +  = ( • )

By formula: Na⁺ + C₁₂H₂₄O₆ = (Na⁺ • C₁₂H₂₄O₆)

Free energy of reaction

 +  = ( • )

By formula: Cs⁺ + C₁₂H₂₄O₆ = (Cs⁺ • C₁₂H₂₄O₆)

 +  = ( • )

By formula: Rb⁺ + C₁₂H₂₄O₆ = (Rb⁺ • C₁₂H₂₄O₆)

 +  = ( • )

By formula: K⁺ + C₁₂H₂₄O₆ = (K⁺ • C₁₂H₂₄O₆)

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Moses and Larson, 1980
Moses, D.J.; Larson, J.W., Electrostatic ring strain in crown ethers, Abstract of papers, 179th ACS National Meeting, Houston, TX, 1980, 984. [all data]

Vasil'ev, Borodin, et al., 1992
Vasil'ev, V.P.; Borodin, V.A.; Kopnyshev, S.B., Standard enthalpies of formation of certain crown-ethers, Russ. J. Phys. Chem. (Engl. Transl.), 1992, 66, 585-587, In original 1104. [all data]

Meot-Ner (Mautner), 1983
Meot-Ner (Mautner), M., The Ionic Hydrogen Bond. 3. Multiple and -CH+...O- Bonds. Complexes of Ammonium Ions with Polyethers and Crown Ethers, J. Am. Chem. Soc., 1983, 105, 15, 4912, https://doi.org/10.1021/ja00353a012 . [all data]

Rodgers and Armentrout, 2000
Rodgers, M.T.; Armentrout, P.B., Noncovalent Metal-Ligand Bond Energies as Studied by Threshold Collision-Induced Dissociation, Mass Spectrom. Rev., 2000, 19, 4, 215, https://doi.org/10.1002/1098-2787(200007)19:4<215::AID-MAS2>3.0.CO;2-X . [all data]

More, Ray, et al., 1999
More, M.B.; Ray, D.; Armentrout, P.B., Intrinsic Affinities of Alkali Cations for 15-Crown-5 and 18-Crown-6: Bond Dissociation Energies of Gas-Phase M+-Crown Ether Complexes, J. Am. Chem. Soc., 1999, 121, 2, 417, https://doi.org/10.1021/ja9823159 . [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References

• Symbols used in this document:
  

  T	Temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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