12-Crown-4

• Formula: C₈H₁₆O₄
• Molecular weight: 176.2102
• IUPAC Standard InChI: InChI=1S/C8H16O4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h1-8H2 Copy

  
• IUPAC Standard InChIKey: XQQZRZQVBFHBHL-UHFFFAOYSA-N Copy
• CAS Registry Number: 294-93-9
• 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: 1,4,7,10-Tetraoxacyclododecane; 12-Crown-4 ether; Eoct; Ethylene oxide cyclic tetramer
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • Ion clustering data
  • Mass spectrum (electron ionization)
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Gas 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

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:
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

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

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₈H₁₆O₄ = (C₃H₁₀N⁺ • C₈H₁₆O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₄H₅N₂⁺ +  = (C₄H₅N₂⁺ • )

By formula: C₄H₅N₂⁺ + C₈H₁₆O₄ = (C₄H₅N₂⁺ • C₈H₁₆O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₅H₆N⁺ +  = (C₅H₆N⁺ • )

By formula: C₅H₆N⁺ + C₈H₁₆O₄ = (C₅H₆N⁺ • C₈H₁₆O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₆H₁₄N⁺ +  = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₈H₁₆O₄ = (C₆H₁₄N⁺ • C₈H₁₆O₄)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

 +  = ( • )

By formula: Na⁺ + C₈H₁₆O₄ = (Na⁺ • C₈H₁₆O₄)

 +  = ( • )

By formula: Li⁺ + C₈H₁₆O₄ = (Li⁺ • C₈H₁₆O₄)

 +  = ( • )

By formula: Cs⁺ + C₈H₁₆O₄ = (Cs⁺ • C₈H₁₆O₄)

 +  = ( • )

By formula: Rb⁺ + C₈H₁₆O₄ = (Rb⁺ • C₈H₁₆O₄)

 +  = ( • )

By formula: K⁺ + C₈H₁₆O₄ = (K⁺ • C₈H₁₆O₄)

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

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

Bystrm and Mansson, 1982
Bystrm, K.; Mansson, M., Enthalpies of formation of some cyclic 1,3- and 1,4-Di- and poly-ethers: Thermochemical strain in the -O-C-O and -O-C-C-O- groups, J. Chem. Soc. Perkin Trans. 2, 1982, 565. [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]

Bystr«65533»m and M«65533»nsson, 1982
Bystr«65533»m, Katarina; M«65533»nsson, Margret, Enthalpies of formation of some cyclic 1,3- and 1,4-di- and poly-ethers: thermochemical strain in the ?O?C?O? and ?O?C?C?O? groups, J. Chem. Soc., Perkin Trans. 2, 1982, 5, 565, https://doi.org/10.1039/p29820000565 . [all data]

Domanska, 1998
Domanska, U., Measurement and correlation of the solubility of crown ethers in selected organic solvents, Pol. J. Chem., 1998, 72, 5, 925. [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]

More, Ray, et al., 1997
More, M.B.; Ray, D.; Armentrout, P.B., Cation-ether complexes in the gas phase: Bond dissociation energies of Na+(dimethyl ether)(x), x=1-4; Na+(1,2-dimethoxyethane)(x), x=1 and 2; and Na+(12-crown-4), J. Phys. Chem. AJOURNAL OF PHYSICAL CHEMISTRY A 101 (5): 831-839 JAN 30 1997, 1997, 101, 831. [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]

Notes

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• Symbols used in this document:
  

  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH°	Enthalpy of vaporization at standard conditions

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