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
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Options:
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Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Condensed phase thermochemistry data

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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

Phase change data

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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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Reduced pressure boiling point

Enthalpy of fusion

Reaction thermochemistry data

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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

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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

Ion clustering data

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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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Free energy of reaction

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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

Free energy of reaction

 +  = ( • )

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

IR Spectrum

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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Additional Data

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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]

Dale and Kristiansen, 1972
Dale, J.; Kristiansen, P.O., Macrocyclic Oligo-ethers Related to Ethylene Oxide., Acta Chem. Scand., 1972, 26, 1471, https://doi.org/10.3891/acta.chem.scand.26-1471 . [all data]

Nichols, Orf, et al., 2000
Nichols, Gary; Orf, Jennifer; Reiter, Sarah M.; Chickos, James; Gokel, George W., The vaporization enthalpies of some crown and polyethers by correlation gas chromatography, Thermochimica Acta, 2000, 346, 1-2, 15-28, https://doi.org/10.1016/S0040-6031(99)00405-0 . [all data]

PCR Inc., 1990
PCR Inc., Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [all data]

Dale, Kristiansen, et al., 1972
Dale, Johannes; Kristiansen, Per Olav; Henriksen, Lars; Liaaen-Jensen, S.; Svensson, Sigfrid, Macrocyclic Oligo-ethers Related to Ethylene Oxide., Acta Chem. Scand., 1972, 26, 1471-1478, https://doi.org/10.3891/acta.chem.scand.26-1471 . [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]

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

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• Symbols used in this document:
  

  T	Temperature
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  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
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH°	Enthalpy of vaporization at standard conditions

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