Ethene, ethoxy-

• Formula: C₄H₈O
• Molecular weight: 72.1057
• IUPAC Standard InChI: InChI=1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3 Copy

  
• IUPAC Standard InChIKey: FJKIXWOMBXYWOQ-UHFFFAOYSA-N Copy
• CAS Registry Number: 109-92-2
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Vinamar; Ether, ethyl vinyl; Ethoxyethene; Ethoxyethylene; Ethyl vinyl ether; EVE; Vinyl ethyl ether; 1-Ethoxyethene; CH2=CHOC2H5; Ethyl ethenyl ether; Ether, vinyl ethyl; 1-Ethoxyethylene; Ethyloxyethene; NSC 8405; ((Vinyl)oxy)ethane
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• Information on this page:
  • Gas phase thermochemistry data
  • 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
• 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

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 by: 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

 +  =

By formula: C₄H₈O + H₂ = C₄H₁₀O

=  + 

By formula: C₄H₉ClO = C₄H₈O + HCl

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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₄H₈O⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% IN CCl4 FOR 4000-1340 CM^-1, 10% IN CS2 FOR 1340-600 CM^-1); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, polar column, isothermal

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

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes

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

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]

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

Favorskii and Shostakovskii, 1943
Favorskii, A.E.; Shostakovskii, M.F., Vinyl ethers. I. Synthesis and properties of vinyl ethers, Zh. Obshch. Kim., 1943, 13, 1-20. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Farchan Laboratories, 1990
Farchan Laboratories, Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [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]

Owen and Sorensen, 1979
Owen, N.L.; Sorensen, G.O., Microwave spectrum, conformation, and barrier to internal rotation of ethyl vinyl ether, J. Phys. Chem., 1979, 83, 1483. [all data]

Dolliver, Gresham, et al., 1938, 2
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. [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]

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]

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]

Failes and Stimson, 1967
Failes, R.L.; Stimson, V.R., The thermal decomposition of 1-ethoxyethyl chloride and the reverse combination, Aust. J. Chem., 1967, 20, 1553-1560. [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]

Morizur, Mercier, et al., 1982
Morizur, J.-P.; Mercier, J.; Sarraf, M., 2-Substituted-2,3-dihydro-4H-pyrans: Competition between 'Retro Diels-Alder' fragmentation and substituent loss, Org. Mass Spectrom., 1982, 17, 327. [all data]

Burgers and Holmes, 1982
Burgers, P.C.; Holmes, J.L., Metastable ion studies. XIII. The measurement of appearance energies of metastable peaks, Org. Mass Spectrom., 1982, 17, 123. [all data]

Holmes, Terlouw, et al., 1976
Holmes, J.L.; Terlouw, J.K.; Lossing, F.P., The thermochemistry of C₂H₄O⁺ ions, J. Phys. Chem., 1976, 80, 2860. [all data]

García-Raso, Martínez-Castro, et al., 1987
García-Raso, A.; Martínez-Castro, I.; Páez, M.I.; Sanz, J.; García-Raso, J.; Saura-Calixto, F., Gas Chromatographic Behaviour of Carbohydrate Trimethylsilyl Ethers. I. Aldopentoses, J. Chromatogr., 1987, 398, 9-20, https://doi.org/10.1016/S0021-9673(01)96491-X . [all data]

Becerra, Sánchez, et al., 1982
Becerra, M.R.; Sánchez, E.F.; Domínguez, J.A.G.; Muñoz, J.G.; Molera, M.J., The use of gaseous and liquid n-paraffins in GC identification of oxidation products of acetondimethyl acetal, J. Chromatogr. Sci., 1982, 20, 8, 363-366, https://doi.org/10.1093/chromsci/20.8.363 . [all data]

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

Golovnya, Misharina, et al., 1978
Golovnya, R.V.; Misharina, T.A.; Garbuzov, V.G., Gas chromatographic characterization of sulfur-containing compounds. 4. The effect of unsaturated radicals on the retention indices of the vinyl, allyl, and propargyl alkyl sulfides, Izv. Akad. Nauk SSSR Ser. Khim., 1978, 11, 2266-2270. [all data]

Zenkevich, 1999
Zenkevich, I.G., New Application of the Retention Index Concept in Gas and High Performance Liquid Chromatography, Fresenius' J. Anal. Chem., 1999, 365, 4, 305-309, https://doi.org/10.1007/s002160051491 . [all data]

Zenkevich, 1997
Zenkevich, I.G., Influence of the Variations of Dynamics Molecular Parameterts on the Additivity of Chromatigraphic Retention Indices of Products of Organic Reactions Relative to Initial Reagents, Dokl. Akad. Nauk (Rus.), 1997, 353, 5, 625-627. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  ΔcH°gas	Enthalpy of combustion of gas at standard conditions
  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
  ΔrH°	Enthalpy 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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