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:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
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Reaction thermochemistry data

Go To: Top, Gas phase ion energetics 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)

Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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

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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Baker, Armen, et al., 1983
Baker, A.D.; Armen, G.H.; Funaro, S., Oral levels of crown ethers and related macrocycles studies by ultraviolet photoelectron spectroscopy: Relationship to complexation studies, J. Chem. Soc. Dalton Trans., 1983, 2519. [all data]

Kajitani, Sugimori, et al., 1979
Kajitani, M.; Sugimori, A.; Sato, N.; Seki, K.; Inokuchi, H.; Harada, Y., Ultraviolet photoelectron spectra of crown ethers, Bull. Chem. Soc. Jpn., 1979, 52, 2199. [all data]

Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  T	Temperature
  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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