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

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

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

Gas Chromatography

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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

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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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.

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]

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]

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

Olson, Wong, et al., 1987
Olson, K.L.; Wong, C.A.; Fleck, L.L.; Lazar, D.F., Qualitative and Quantitative Determination of Solvent Formulations in Automotive Paints, J. Chromatogr. Sci., 1987, 25, 9, 418-423, https://doi.org/10.1093/chromsci/25.9.418 . [all data]

Olson, Wong, et al., 1988
Olson, K.L.; Wong, C.A.; Fleck, L.L.; Lazar, D.F., Qualitative and quantitative determination of solvent formulations in automotive paints, J. Coat. Technol., 1988, 60, 762, 45-50. [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°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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