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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

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

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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:
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

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

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

CH₆N⁺ +  = (CH₆N⁺ • )

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

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

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

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

Free energy of reaction

C₄H₁₁O⁺ +  = (C₄H₁₁O⁺ • )

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

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

C₅H₆N⁺ +  = (C₅H₆N⁺ • )

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

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

C₅H₁₁O⁺ +  = (C₅H₁₁O⁺ • )

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

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

C₆H₁₄N⁺ +  = (C₆H₁₄N⁺ • )

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

Bond type: Hydrogen bonds of the type NH+-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

 +  = C₄H₁₀ClO^-

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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

Free energy of reaction

( • ) +  = ( • 2)

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

( • 2) +  = ( • 3)

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

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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, polar column, isothermal

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Kovats' RI, polar column, temperature ramp

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

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, isothermal

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, Notes

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

Pihlaja and Heikkil, 1968
Pihlaja, K.; Heikkil, J., Heats of combustion. Diethyl ether and 1,1-diethoxyethane, Acta Chem. Scand., 1968, 22, 2731-2732. [all data]

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Pilcher, Skinner, et al., 1963
Pilcher, G.; Skinner, H.A.; Pell, A.S.; Pope, A.E., Measurements of heats of combustion by flame calorimetry. Part 1.-Diethyl ether, ethyl vinyl ether and divinyl ether, Trans. Faraday Soc., 1963, 59, 316-330. [all data]

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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 J.F., 1971
Counsell J.F., Thermodynamic properties of organic oxygen compounds. Part XXVI. Diethyl ether, J. Chem. Soc. A, 1971, 313-316. [all data]

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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]

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Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, References

• Symbols used in this document:
  

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