Ethane, 1,1'-oxybis[2-methoxy-

• Formula: C₆H₁₄O₃
• Molecular weight: 134.1736
• IUPAC Standard InChI: InChI=1S/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: SBZXBUIDTXKZTM-UHFFFAOYSA-N Copy
• CAS Registry Number: 111-96-6
• 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: Ether, bis(2-methoxyethyl); (2-Methoxyethyl) ether; Bis(2-methoxyethyl) ether; Di(2-Methoxyethyl) ether; Diethylene glycol dimethyl ether; Diglyme; Dimethyl carbitol; Ethanol, 2,2'-oxybis-, dimethyl ether; Glyme-2; Poly-Solv; 2-(2-Methoxyethoxy)-1-methoxyethane; 2,5,8-Trioxanonane; CH3OCH2CH2OCH2CH2OCH3; Dimethoxydiethylene glycol; Dimethyldigol; Diethyl glycol dimethyl ether; 1,1'-Oxybis(2-methoxy)ethane; 2,2'-Oxybisethanol dimethyl ether; Diglycol methyl ether; NSC 59726; Methyl diglyme; diglyme (diethylene glycol dimethyl ether)
• 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
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
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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 as indicated in comments:
DRB - Donald R. Burgess, Jr.

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

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
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of fusion

Entropy 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

 +  = ( • )

By formula: C₂H₃O₂^- + C₆H₁₄O₃ = (C₂H₃O₂^- • C₆H₁₄O₃)

(C₆H₁₅O₃⁺ • ) +  = (C₆H₁₅O₃⁺ •  • )

By formula: (C₆H₁₅O₃⁺ • H₃N) + C₆H₁₄O₃ = (C₆H₁₅O₃⁺ • C₆H₁₄O₃ • H₃N)

Bond type: Hydrogen bonds between protonated and neutral organics

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₆H₁₄O₃ = (C₃H₁₀N⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₄H₅N₂⁺ +  = (C₄H₅N₂⁺ • )

By formula: C₄H₅N₂⁺ + C₆H₁₄O₃ = (C₄H₅N₂⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₅H₅FN⁺ +  = (C₅H₅FN⁺ • )

By formula: C₅H₅FN⁺ + C₆H₁₄O₃ = (C₅H₅FN⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₅H₆N⁺ +  = (C₅H₆N⁺ • )

By formula: C₅H₆N⁺ + C₆H₁₄O₃ = (C₅H₆N⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₆H₁₄N⁺ +  = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₆H₁₄O₃ = (C₆H₁₄N⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

(C₆H₁₅O₃⁺ • ) +  = (C₆H₁₅O₃⁺ •  • )

By formula: (C₆H₁₅O₃⁺ • C₆H₁₄O₃) + H₂O = (C₆H₁₅O₃⁺ • H₂O • C₆H₁₄O₃)

Bond type: Hydrogen bond (positive ion to hydride)

C₆H₁₅O₃⁺ +  = (C₆H₁₅O₃⁺ • )

By formula: C₆H₁₅O₃⁺ + C₆H₁₄O₃ = (C₆H₁₅O₃⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds between protonated and neutral organics

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

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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

 +  = ( • )

By formula: C₂H₃O₂^- + C₆H₁₄O₃ = (C₂H₃O₂^- • C₆H₁₄O₃)

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₆H₁₄O₃ = (C₃H₁₀N⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₄H₅N₂⁺ +  = (C₄H₅N₂⁺ • )

By formula: C₄H₅N₂⁺ + C₆H₁₄O₃ = (C₄H₅N₂⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₅H₅FN⁺ +  = (C₅H₅FN⁺ • )

By formula: C₅H₅FN⁺ + C₆H₁₄O₃ = (C₅H₅FN⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₅H₆N⁺ +  = (C₅H₆N⁺ • )

By formula: C₅H₆N⁺ + C₆H₁₄O₃ = (C₅H₆N⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₆H₁₄N⁺ +  = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₆H₁₄O₃ = (C₆H₁₄N⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₆H₁₅O₃⁺ +  = (C₆H₁₅O₃⁺ • )

By formula: C₆H₁₅O₃⁺ + C₆H₁₄O₃ = (C₆H₁₅O₃⁺ • C₆H₁₄O₃)

Bond type: Hydrogen bonds between protonated and neutral organics

(C₆H₁₅O₃⁺ • ) +  = (C₆H₁₅O₃⁺ •  • )

By formula: (C₆H₁₅O₃⁺ • H₃N) + C₆H₁₄O₃ = (C₆H₁₅O₃⁺ • C₆H₁₄O₃ • H₃N)

Bond type: Hydrogen bonds between protonated and neutral organics

References

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

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

Stewart, 2004
Stewart, J.J.P., Comparison of the accuracy of semiempirical and some DFT methods for predicting heats of formation, J. Mol. Model, 2004, 10, 1, 6-10, https://doi.org/10.1007/s00894-003-0157-6 . [all data]

Gutner, Lebedeva, et al., 1980
Gutner, N.M.; Lebedeva, N.D.; Dobychin, S.L.; Kiseleva, N.N., Thermochemical study of aliphatic ethers, J. Appl. Chem. USSR, 1980, 53, 1523-1525. [all data]

Mansson, 1969
Mansson, M., Non-bonded oxygen-oxygen interactions in straight-chain compounds, J. Chem. Thermodyn., 1969, 1, 141-151. [all data]

Baroody and Carpenter, 1972
Baroody, E.E.; Carpenter, G.A., Heats of formation of propellant compounds (U), Rpt. Naval Ordnance Systems Command Task No. 331-003/067-1/UR2402-001 for Naval Ordance Station, Indian Head, MD, 1972, 1-9. [all data]

Beaumont, Clegg, et al., 1966
Beaumont, R.H.; Clegg, B.; Gee, G.; Herbert, J.B.M.; Marks, D.J.; Roberts, R.C.; Sims, D., Heat capacities of propylene oxide and of some polymers of ethylene and propylene oxides, Polymer, 1966, 7, 401-416. [all data]

Trejo, Costas, et al., 1991
Trejo, L.M.; Costas, M.; Patterson, D., Excess heat capacity of organic mixtures, Internat. DATA Series, Selected Data Mixt., 1991, Ser. [all data]

Villamanan, Casanova, et al., 1982
Villamanan, M.A.; Casanova, C.; Roux-Desgranges, G.; Grolier, J.-P.E., Thermochemical behavior of mixtures of n-alcohol + aliphatic ether: heat capacities and volumes at 298.15 K, Thermochim. Acta, 1982, 52, 279-283. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Anonymous, 1982
Anonymous, X., Glymes Grant Chemical, 1982, Baton Rouge, LA 1982. [all data]

Wallace and Mathews, 1964
Wallace, W.J.; Mathews, A.L., Density, Refractive Indices, Molar Refractions, and Viscosities of Diethylene Glycol Dimethyl Ether-Water Solutions at 25 C, J. Chem. Eng. Data, 1964, 9, 267-268. [all data]

Beaumont, Clegg, et al., 1966, 2
Beaumont, R.H.; Clegg, B.; Gee, G.; Herbert, J.B.M.; Marks, D.J.; Roberts, R.C.; Sims, D., Heat Capacities of Propylene Oxide and of Some Polymers of Ethylene and Propylene Oxides, Polymer, 1966, 7, 401. [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]

Li, Fang, et al., 2009
Li, Dan; Fang, Wenjun; Xie, Wenjie; Xing, Yan; Guo, Yongsheng; Lin, Ruisen, Measurements on Vapor Pressure and Thermal Conductivity for Pseudo-binary Systems of a Hydrocarbon Fuel with Ethylene and Diethylene Glycol Dimethyl Ethers, Energy Fuels, 2009, 23, 2, 794-798, https://doi.org/10.1021/ef8007163 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Meot-Ner and Sieck, 1986
Meot-Ner, M.; Sieck, L.W., The ionic hydrogen bond and ion solvation. 5. OH...O^- bonds. Gas phase solvation and clustering of alkoxide and carboxylate anions, J. Am. Chem. Soc., 1986, 108, 7525. [all data]

Meot-Ner (Mautner), Sieck, et al., 1996
Meot-Ner (Mautner), M.; Sieck, L.W.; Liebman, J.F.; Scheiner, S., Complexing of the Ammonium Ion by Polyethers. Comparative Complexing Thermochemistry of Ammonium, Hydronium, and Alkali Cations, J. Phys. Chem., 1996, 100, 16, 6445, https://doi.org/10.1021/jp9514943 . [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]

Meot-Ner (Mautner), Sieck, et al., 1994
Meot-Ner (Mautner), M.; Sieck, L.W.; Liebman, J.F.; Scheiner, S.; Duan, X., The Ionic Hydrogen Bond. 5. Polydentate and Solvent-Bridged Structures. Complexing of the Proton and the Hydronium Ions by Polyethers, J. Am. Chem. Soc., 1994, 116, 17, 7848, https://doi.org/10.1021/ja00096a047 . [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]

Notes

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• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  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
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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