Ethyl ether

• Formula: C₄H₁₀O
• Molecular weight: 74.1216
• IUPAC Standard InChI: InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: RTZKZFJDLAIYFH-UHFFFAOYSA-N Copy
• CAS Registry Number: 60-29-7
• 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: Ethane, 1,1'-oxybis-; Anaesthetic ether; Anesthesia ether; Anesthetic ether; Diethyl ether; Diethyl oxide; Ethoxyethane; Pronarcol; Solvent ether; 1,1'-Oxybisethane; (C2H5)2O; Aether; Diaethylaether; Dwuetylowy eter; Etere etilico; Ether ethylique; Ether, ethyl; Ethyl ether, tech.; Ethyl oxide; Oxyde d'ethyle; Rcra waste number U117; UN 1155; 3-Oxapentane; Ether; Ethyl ether anhydrous A.C.S.; Sulfuric ether; NSC 100036
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• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
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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

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar
B - John E. Bartmess

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

C₄H₁₁O⁺ +  = (C₄H₁₁O⁺ • )

By formula: C₄H₁₁O⁺ + C₄H₁₀O = (C₄H₁₁O⁺ • C₄H₁₀O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₅H₁₁O⁺ +  = (C₅H₁₁O⁺ • )

By formula: C₅H₁₁O⁺ + C₄H₁₀O = (C₅H₁₁O⁺ • C₄H₁₀O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₆H₁₅O⁺ +  = (C₆H₁₅O⁺ • )

By formula: C₆H₁₅O⁺ + C₄H₁₀O = (C₆H₁₅O⁺ • C₄H₁₀O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₆H₁₅O⁺ +  = (C₆H₁₅O⁺ • )

By formula: C₆H₁₅O⁺ + C₄H₁₀O = (C₆H₁₅O⁺ • C₄H₁₀O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + C₄H₁₀O = (C₃H₉Si⁺ • C₄H₁₀O)

Free energy of reaction

C₆H₁₄N⁺ +  = (C₆H₁₄N⁺ • )

By formula: C₆H₁₄N⁺ + C₄H₁₀O = (C₆H₁₄N⁺ • C₄H₁₀O)

Bond type: Hydrogen bonds of the type NH+-O between organics

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₄H₁₀O = (CH₆N⁺ • C₄H₁₀O)

Bond type: Hydrogen bonds of the type NH+-O between organics

 +  =

By formula: C₄H₈O + H₂ = C₄H₁₀O

 +  = ( • )

By formula: Na⁺ + C₄H₁₀O = (Na⁺ • C₄H₁₀O)

Free energy of reaction

C₅H₆N⁺ +  = (C₅H₆N⁺ • )

By formula: C₅H₆N⁺ + C₄H₁₀O = (C₅H₆N⁺ • C₄H₁₀O)

Bond type: Hydrogen bonds of the type NH+-O between organics

 +  = ( • )

By formula: NO^- + C₄H₁₀O = (NO^- • C₄H₁₀O)

 + 2 =

By formula: C₄H₆O + 2H₂ = C₄H₁₀O

 +  = C₄H₁₀ClO^-

By formula: Cl^- + C₄H₁₀O = C₄H₁₀ClO^-

( • 2) +  = ( • 3)

By formula: (Na⁺ • 2C₄H₁₀O) + C₄H₁₀O = (Na⁺ • 3C₄H₁₀O)

( • ) +  = ( • 2)

By formula: (Na⁺ • C₄H₁₀O) + C₄H₁₀O = (Na⁺ • 2C₄H₁₀O)

 +  = ( • )

By formula: K⁺ + C₄H₁₀O = (K⁺ • C₄H₁₀O)

 +  = ( • )

By formula: Mg⁺ + C₄H₁₀O = (Mg⁺ • C₄H₁₀O)

2 =  + 

By formula: 2C₂H₆O = C₄H₁₀O + H₂O

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References, Notes

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:
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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Appearance energy determinations

References

Go To: Top, Condensed phase thermochemistry 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.

Murrin and Goldhagen, 1957
Murrin, J.W.; Goldhagen, S., Determination of the C-O bond energy from the heats of combustion of four aliphatic ethers, NAVORD Report No. 5491, U.S. Naval Powder Factory Res. & Dev. Dept., 1957, 1-14. [all data]

Counsell, Lee, et al., 1971
Counsell, J.F.; Lee, D.A.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XXVI. Diethyl ether, 1971, J. [all data]

Parks, Kelley, et al., 1929
Parks, G.S.; Kelley, K.K.; Huffman, H.M., Thermal data on organic compounds. V. A revision of the entropies and free energies of nineteen organic compounds, J. Am. Chem. Soc., 1929, 51, 1969-1973. [all data]

Parks and Huffman, 1926
Parks, G.S.; Huffman, H.M., Thermal data on organic compounds. IV. The heat capacities, entropies and free energies of normal propyl alcohol, ethyl ether and dulcitol, J. Am. Chem. Soc., 1926, 48, 2788-2793. [all data]

Mazur, 1939
Mazur, J., Über die spezifische Wärme des Äthyläthers, Acta Phys. Pol., 1939, 7, 318-326. [all data]

Mazur, 1939, 2
Mazur, J., Über die spezifische Wärme des Äthyläthers, des Nitrobenzols und des Schwefelkohlenstoffs, Z. Physik., 1939, 113, 710-720. [all data]

Kurnakov and Voskresenskaya, 1936
Kurnakov, N.S.; Voskresenskaya, N.K., Calorimetry of liquid binary systems, Izv. Akad. Nauk SSSR, Otdel. Mat. i Estestv. Nauk. Ser. Khim, 1936, 1936, 439-461. [all data]

Aoyama and Kanda, 1935
Aoyama, S.; Kanda, E., Studies on the heat capacities at low temperature. Report I. Heat capacities of some organic substances at low temperature, Sci. Rept. Tohoku Imp. Univ. [1]24, 1935, 107-115. [all data]

Bennewitz and Wendroth, 1927
Bennewitz, K.; Wendroth, H., Untersuchungen im kritischen Gebiet. II. Bestimmung der wahren spezifischen Wärme Cp des flüssigne Äthyläthers oberund unterhalb der kritischen Temperatur, Z. Phys. Chem., 1927, 125, 111-134. [all data]

Keyes and Beattie, 1924
Keyes, F.G.; Beattie, J.A., A calorimeter for measuring specific heats and heats of vaporization of liquids. The specific heat and heat of vaporization of liquid ethyl ether at 0° and 12°, J. Am. Chem. Soc., 1924, 46, 1753-1760. [all data]

Szulejko and McMahon, 1991
Szulejko, J.E.; McMahon, T.B., A Pulsed Electron Beam, Variable Temperature, High Pressure Mass Spectrometric Reevaluation of the Proton Affinity Difference Between 2-Methylpropene and Ammonia, Int. J. Mass Spectrom. Ion Proc., 1991, 109, 279, https://doi.org/10.1016/0168-1176(91)85109-Y . [all data]

Larson and McMahon, 1982
Larson, J.W.; McMahon, T.B., Formation, Thermochemistry, and Relative Stabilities of Proton - Bound dimers of Oxygen n - Donor Bases from Ion Cyclotron Resonance Solvent - Exchange Equilibria Measurements, J. Am. Chem. Soc., 1982, 104, 23, 6255, https://doi.org/10.1021/ja00387a016 . [all data]

Grimsrud and Kebarle, 1973
Grimsrud, E.P.; Kebarle, P., Gas Phase Ion Equilibria Studies of the Solvation of the Hydrogen Ion by Methanol, Dimethyl Ether and Water. Effect of Hydrogen Bonding, J. Am. Chem. Soc., 1973, 95, 24, 7939, https://doi.org/10.1021/ja00805a002 . [all data]

Lias, Liebman, et al., 1984
Lias, S.G.; Liebman, J.F.; Levin, R.D., Evaluated gas phase basicities and proton affinities of molecules heats of formation of protonated molecules, J. Phys. Chem. Ref. Data, 1984, 13, 695. [all data]

Keesee and Castleman, 1986
Keesee, R.G.; Castleman, A.W., Jr., Thermochemical data on Ggs-phase ion-molecule association and clustering reactions, J. Phys. Chem. Ref. Data, 1986, 15, 1011. [all data]

Wojtyniak and Stone, 1986
Wojtyniak, A.C.M.; Stone, A.J., A High-Pressure Mass Spectrometric Study of the Bonding of Trimethylsilylium to Oxygen and Aromatic Bases, Can. J. Chem., 1986, 74, 59. [all data]

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [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]

Allinger, Glaser, et al., 1981
Allinger, N.L.; Glaser, J.A.; Davis, H.E., Heats of hydrogenation of some vinyl ethers and related compounds, J. Org. Chem., 1981, 46, 658-661. [all data]

Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E., Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds, J. Am. Chem. Soc., 1938, 60, 440-450. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Guo, Conklin, et al., 1989
Guo, B.C.; Conklin, B.J.; Castleman, A.W., Thermochemical Properties of Ion Complexes Na+(M)n in the Gas Phase, J. Am. Chem. Soc., 1989, 111, 17, 6506, https://doi.org/10.1021/ja00199a005 . [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]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]

Bogdanov, Lee, et al., 2001
Bogdanov, B.; Lee, H.J.S.; McMahon, T.B., Influence of fluorine substitution on the structures and thermochemistry of chloride ion-ether complexes in the gas phase, Int. J. Mass Spectrom., 2001, 210, 387-402, https://doi.org/10.1016/S1387-3806(01)00404-3 . [all data]

Davidson and Kebarle, 1976
Davidson, W.R.; Kebarle, P., Binding Energies and Stabilities of Potassium Ion Complexes from Studies of Gas Phase Ion Equilibria K+ + M = K+.M, J. Am. Chem. Soc., 1976, 98, 20, 6133, https://doi.org/10.1021/ja00436a011 . [all data]

Operti, Tews, et al., 1988
Operti, L.; Tews, E.C.; Freiser, B.S., Determination of Gas-Phase Ligand Binding Energies to Mg+ by FTMS Techniques, J. Am. Chem. Soc., 1988, 110, 12, 3847, https://doi.org/10.1021/ja00220a020 . [all data]

Connett, 1972
Connett, J.E., Chemical equilibria 4. Enthalpy of dehydration of ethanol to diethyl ether by measurement of equilibrium constants in ethanol + ether+ water by a vapour flow technique, J. Chem. Thermodyn., 1972, 4, 135-138. [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]

Bowen and Maccoll, 1984
Bowen, R.D.; Maccoll, A., Low energy, low temperature mass spectra, Org. Mass Spectrom., 1984, 19, 379. [all data]

Botter, Pechine, et al., 1977
Botter, R.; Pechine, J.M.; Rosenstock, H.M., Photoionization of dimethyl ether and diethyl ether, Int. J. Mass Spectrom. Ion Phys., 1977, 25, 7. [all data]

Behan, Dean, et al., 1976
Behan, J.M.; Dean, F.M.; Johnstone, R.A.W., Photoelectron spectra of cyclic aromatic ethers. The question of the Mills-Nixon effect, Tetrahedron, 1976, 32, 167. [all data]

Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J., The effect of alkyl substitution on ionisation potential, J. Chem. Soc., 1971, (B), 790. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Ohno, Imai, et al., 1985
Ohno, K.; Imai, K.; Harada, Y., Variations in reactivity of lone-pair electrons due to intramolecular hydrogen bonding as observed by penning ionization electron spectroscopy, J. Am. Chem. Soc., 1985, 107, 8078. [all data]

Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T., Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]

Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [all data]

Aue, Webb, et al., 1975
Aue, D.H.; Webb, H.M.; Bowers, M.T., Proton affinities, ionization potentials, and hydrogen affinities of nitrogen and oxygen bases. Hybridization effects, J. Am. Chem. Soc., 1975, 97, 4137. [all data]

Selim and Helal, 1981
Selim, E.T.M.; Helal, A.I., Heat of formation of CH₂=OH⁺ fragment ion, Indian J. Pure Appl. Phys., 1981, 19, 977. [all data]

Holmes, Rye, et al., 1979
Holmes, J.L.; Rye, R.T.B.; Terlouw, J.K., On the loss of ethylene from [C₃H₇O]⁺ ions of structure CH₃CH₂CHOH, Org. Mass Spectrom., 1979, 14, 606. [all data]

Harrison, Ivko, et al., 1966
Harrison, A.G.; Ivko, A.; Van Raalte, D., Energetics of formation of some oxygenated ions and the proton affinities of carbonyl compounds, Can. J. Chem., 1966, 44, 1625. [all data]

Williams and Hamill, 1968
Williams, J.M.; Hamill, W.H., Ionization potentials of molecules and free radicals and appearance potentials by electron impact in the mass spectrometer, J. Chem. Phys., 1968, 49, 4467. [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]

Phillips, Russell, et al., 1975
Phillips, G.R.; Russell, M.E.; Solka, B.H., The structure of the [C₂H₅O]⁺ ion in the mass spectrum of diethyl ether, Org. Mass Spectrom., 1975, 10, 819. [all data]

Tsang and Harrison, 1970
Tsang, C.W.; Harrison, A.G., Four-centred rearrangements in the mass spectra of aliphatic ethers, Org. Mass Spectrom., 1970, 3, 647. [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

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