Ethane, 1,2-dimethoxy-

• Formula: C₄H₁₀O₂
• Molecular weight: 90.1210
• IUPAC Standard InChI: InChI=1S/C4H10O2/c1-5-3-4-6-2/h3-4H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: XTHFKEDIFFGKHM-UHFFFAOYSA-N Copy
• CAS Registry Number: 110-71-4
• 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: α,β-Dimethoxyethane; Dimethoxyethane; Dimethyl cellosolve; Ethylene dimethyl ether; Ethylene glycol dimethyl ether; Glycol dimethyl ether; Glyme; Monoethylene glycol dimethyl ether; Monoglyme; 1,2-Dimethoxyethane; 1,2-Ethanediol dimethyl ether; 2,5-Dioxahexane; CH3OCH2CH2OCH3; Egdme; UN 2252; Ansul ether 121; DME; DME (glycol ether); Hisolve MMM; NSC 60542
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Antoine Equation Parameters

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

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Reaction thermochemistry data

Go To: Top, Phase change data, 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

(C₄H₁₁O₂⁺ • 2 • 2) +  = (C₄H₁₁O₂⁺ • 3 • 2)

By formula: (C₄H₁₁O₂⁺ • 2H₂O • 2C₄H₁₀O₂) + H₂O = (C₄H₁₁O₂⁺ • 3H₂O • 2C₄H₁₀O₂)

Bond type: Hydrogen bond (positive ion to hydride)

Free energy of reaction

(C₄H₁₁O₂⁺ • 3 • ) +  = (C₄H₁₁O₂⁺ • 4 • )

By formula: (C₄H₁₁O₂⁺ • 3H₂O • C₄H₁₀O₂) + H₂O = (C₄H₁₁O₂⁺ • 4H₂O • C₄H₁₀O₂)

Bond type: Hydrogen bond (positive ion to hydride)

Free energy of reaction

(C₄H₁₁O₂⁺ • 2) +  = (C₄H₁₁O₂⁺ • 3)

By formula: (C₄H₁₁O₂⁺ • 2C₄H₁₀O₂) + C₄H₁₀O₂ = (C₄H₁₁O₂⁺ • 3C₄H₁₀O₂)

Bond type: Hydrogen bonds between protonated and neutral organics

Free energy of reaction

 +  = ( • )

By formula: Na⁺ + C₄H₁₀O₂ = (Na⁺ • C₄H₁₀O₂)

Free energy of reaction

 +  = ( • )

By formula: K⁺ + C₄H₁₀O₂ = (K⁺ • C₄H₁₀O₂)

Bond type: Polydentate bonding in non-hydrogen-bonded positive ions

( • ) +  = ( • 2)

By formula: (Na⁺ • C₄H₁₀O₂) + C₄H₁₀O₂ = (Na⁺ • 2C₄H₁₀O₂)

(C₄H₁₁O₂⁺ •  • 2) +  = (C₄H₁₁O₂⁺ • 2 • 2)

By formula: (C₄H₁₁O₂⁺ • C₄H₁₀O₂ • 2H₂O) + C₄H₁₀O₂ = (C₄H₁₁O₂⁺ • 2C₄H₁₀O₂ • 2H₂O)

Bond type: Hydrogen bonds between protonated and neutral organics

(C₄H₁₁O₂⁺ • 2 • ) +  = (C₄H₁₁O₂⁺ • 3 • )

By formula: (C₄H₁₁O₂⁺ • 2H₂O • C₄H₁₀O₂) + H₂O = (C₄H₁₁O₂⁺ • 3H₂O • C₄H₁₀O₂)

Bond type: Hydrogen bond (positive ion to hydride)

(C₄H₁₁O₂⁺ •  • 2) +  = (C₄H₁₁O₂⁺ • 2 • 2)

By formula: (C₄H₁₁O₂⁺ • H₂O • 2C₄H₁₀O₂) + H₂O = (C₄H₁₁O₂⁺ • 2H₂O • 2C₄H₁₀O₂)

Bond type: Hydrogen bond (positive ion to hydride)

(C₄H₁₁O₂⁺ •  • ) +  = (C₄H₁₁O₂⁺ • 2 • )

By formula: (C₄H₁₁O₂⁺ • H₂O • C₄H₁₀O₂) + H₂O = (C₄H₁₁O₂⁺ • 2H₂O • C₄H₁₀O₂)

Bond type: Hydrogen bond (positive ion to hydride)

C₅H₆N⁺ +  = (C₅H₆N⁺ • )

By formula: C₅H₆N⁺ + C₄H₁₀O₂ = (C₅H₆N⁺ • C₄H₁₀O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

( • ) +  = ( •  • )

By formula: (H₄N⁺ • C₄H₁₀O₂) + H₃N = (H₄N⁺ • H₃N • C₄H₁₀O₂)

Bond type: Hydrogen bond (positive ion to hydride)

(C₄H₁₁O₂⁺ • ) +  = (C₄H₁₁O₂⁺ •  • )

By formula: (C₄H₁₁O₂⁺ • C₄H₁₀O₂) + H₂O = (C₄H₁₁O₂⁺ • H₂O • C₄H₁₀O₂)

Bond type: Hydrogen bond (positive ion to hydride)

C₄H₁₁O₂⁺ +  = (C₄H₁₁O₂⁺ • )

By formula: C₄H₁₁O₂⁺ + C₄H₁₀O₂ = (C₄H₁₁O₂⁺ • C₄H₁₀O₂)

Bond type: Hydrogen bonds between protonated and neutral organics

 +  = ( • )

By formula: H₄N⁺ + C₄H₁₀O₂ = (H₄N⁺ • C₄H₁₀O₂)

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₄H₁₀O₂ = (C₃H₁₀N⁺ • C₄H₁₀O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

C₆H₁₄N⁺ +  = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₄H₁₀O₂ = (C₆H₁₄N⁺ • C₄H₁₀O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₄H₁₀O₂ = (CH₆N⁺ • C₄H₁₀O₂)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

( • 2) +  = ( • 3)

By formula: (H₄N⁺ • 2C₄H₁₀O₂) + C₄H₁₀O₂ = (H₄N⁺ • 3C₄H₁₀O₂)

( • ) +  = ( • 2)

By formula: (H₄N⁺ • C₄H₁₀O₂) + C₄H₁₀O₂ = (H₄N⁺ • 2C₄H₁₀O₂)

( • 2) +  = ( • 3)

By formula: (Na⁺ • 2C₄H₁₀O₂) + C₄H₁₀O₂ = (Na⁺ • 3C₄H₁₀O₂)

 +  = 2 + 

By formula: C₄H₁₀O₂ + H₂O = 2CH₄O + C₂H₄O

2 +  =  + 

By formula: 2CH₄O + C₂H₄O = C₄H₁₀O₂ + H₂O

( • ) +  = ( • 2)

By formula: (Li⁺ • C₄H₁₀O₂) + C₄H₁₀O₂ = (Li⁺ • 2C₄H₁₀O₂)

( • ) +  = ( • 2)

By formula: (Cs⁺ • C₄H₁₀O₂) + C₄H₁₀O₂ = (Cs⁺ • 2C₄H₁₀O₂)

( • ) +  = ( • 2)

By formula: (Rb⁺ • C₄H₁₀O₂) + C₄H₁₀O₂ = (Rb⁺ • 2C₄H₁₀O₂)

( • ) +  = ( • 2)

By formula: (K⁺ • C₄H₁₀O₂) + C₄H₁₀O₂ = (K⁺ • 2C₄H₁₀O₂)

( • ) +  = ( • 2)

By formula: (Cu⁺ • C₄H₁₀O₂) + C₄H₁₀O₂ = (Cu⁺ • 2C₄H₁₀O₂)

 +  = ( • )

By formula: Li⁺ + C₄H₁₀O₂ = (Li⁺ • C₄H₁₀O₂)

 +  = ( • )

By formula: Cs⁺ + C₄H₁₀O₂ = (Cs⁺ • C₄H₁₀O₂)

 +  = ( • )

By formula: Rb⁺ + C₄H₁₀O₂ = (Rb⁺ • C₄H₁₀O₂)

 +  = ( • )

By formula: Cu⁺ + C₄H₁₀O₂ = (Cu⁺ • C₄H₁₀O₂)

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
L - Sharon G. Lias

Data compiled as indicated in comments:
MM - Michael M. Meot-Ner (Mautner)
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

Proton affinity at 298K

Ionization energy determinations

Appearance energy determinations

References

Go To: Top, Phase change data, 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.

Guanquan, Ott, et al., 1986
Guanquan, C.; Ott, J.B.; Goates, J.R., (Solid+liquid) phase equilibria and solid-compound formation in 1,2-dimethoxyethane+tetrachloromethane, +trichlorofluoromethane, and +trichloromethane, J. Chem. Thermodyn., 1986, 18, 31. [all data]

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

Steele, Chirico, et al., 1996
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K., Thermodynamic properties and ideal-gas enthalpies of formation for butyl vinyl ether, 1,2-dimethoxyethane, methyl glycolate, bicyclo[2.2.1]hept-2-ene, 5-vinylbicyclo[2.2.1]hept-2-ene, trans-azobenzene, butyl acrylate, di-tert-butyl ether, and hexane-1,6-diol, J. Chem. Eng. Data, 1996, 41, 1285-1302. [all data]

Quadri and Kudchadker, 1991
Quadri, S.K.; Kudchadker, A.P., Measurement of the critical temperatures and critical pressures of some thermally stable or mildly unstable esters, ketones, and ethers, J. Chem. Thermodyn., 1991, 23, 129-34. [all data]

Kobe, Ravicz, et al., 1956
Kobe, K.A.; Ravicz, A.E.; Vohra, S.P., Critical Properties and Vapor Pressures of Some Ethers and Heterocyclic Compounds, J. Chem. Eng. Data, 1956, 1, 50. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [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]

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]

Armentrout and Rodgers, 2000
Armentrout, P.B.; Rodgers, M.T., An Absolute Sodium Cation Affinity Scale: Threshold Collision-Induced Dissociation Experiments and ab Initio Theory, J. Phys. Chem A, 2000, 104, 11, 2238, https://doi.org/10.1021/jp991716n . [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., 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]

Castleman, Peterson, et al., 1983
Castleman, A.W.; Peterson, K.I.; Upschulte, B.L.; Schelling, F.J., Energetics and Structure of Na+ Cluster Ions, Int. J. Mass Spectrom. Ion Phys., 1983, 47, 203, https://doi.org/10.1016/0020-7381(83)87171-X . [all data]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]

Davidson and Kebarle, 1976
Davidson, W.R.; Kebarle, P., Binding Energies and Stabilities of Potassium Ion Complexes with Ethylene Diamine and Dimethoxyethane (Glyme) from Measurements of the Complexing Equilibria in the Gas Phase, Can. J. Chem., 1976, 54, 16, 2594, https://doi.org/10.1139/v76-368 . [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., 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]

Wiberg, Morgan, et al., 1994
Wiberg, K.B.; Morgan, K.M.; Maltz, H., Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria, J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]

Koizumi, 2001
Koizumi, H., Collision-Induced Dissociation and Theoretical Studies of Cu+-Dimethoxyethane Complexes, J. Am. Soc. Mass Spectrom., 2001, 12, 5, 480, https://doi.org/10.1016/S1044-0305(01)00242-2 . [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]

Morlender-Vais and Holmes, 2001
Morlender-Vais, N.; Holmes, J.L., Proton affinities of two weakly bidentate molecules: 1,2-Dimethoxyethane and methoxyacetone, Int. J. Mass Spectrom., 2001, 210/211, 147. [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]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Holmes and Lossing, 1984
Holmes, J.L.; Lossing, F.P., Heats of formation of organic radicals from appearance energies, Int. J. Mass Spectrom. Ion Processes, 1984, 58, 113. [all data]

Lossing, 1977
Lossing, F.P., Heats of formation of some isomeric [C_nH_2n+1]⁺ ions. Substitutional effects on ion stability, J. Am. Chem. Soc., 1977, 99, 7526. [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Vc	Critical volume
  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
  ρc	Critical density

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