Ethyl Acetate

• Formula: C₄H₈O₂
• Molecular weight: 88.1051
• IUPAC Standard InChI: InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: XEKOWRVHYACXOJ-UHFFFAOYSA-N Copy
• CAS Registry Number: 141-78-6
• 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: Acetic acid, ethyl ester; Acetic ether; Acetidin; Acetoxyethane; Ethyl acetic ester; Ethyl ethanoate; Vinegar naphtha; CH3COOC2H5; Aethylacetat; Essigester; Ethyle (acetate d'); Etile (acetato di); Ethylacetaat; Ethylester kyseliny octove; Rcra waste number U112; UN 1173; Ethyl ester of acetic acid; 1-Acetoxyethane; NSC 70930; ac. acetic ethyl ester
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Gas Chromatography
• Data at other public NIST sites:
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  • 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Ion clustering data, Mass spectrum (electron ionization), 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:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LL - Sharon G. Lias and Joel F. Liebman
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

View reactions leading to C₄H₈O₂⁺ (ion structure unspecified)

Gas basicity at 298K

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₇O₂^- +  =

By formula: C₄H₇O₂^- + H⁺ = C₄H₈O₂

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 by: 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + C₄H₈O₂ = (C₃H₉Si⁺ • C₄H₈O₂)

Free energy of reaction

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + C₄H₈O₂ = (C₃H₉Sn⁺ • C₄H₈O₂)

Free energy of reaction

C₄H₉O₂⁺ +  = (C₄H₉O₂⁺ • )

By formula: C₄H₉O₂⁺ + C₄H₈O₂ = (C₄H₉O₂⁺ • C₄H₈O₂)

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

 +  = ( • )

By formula: NO^- + C₄H₈O₂ = (NO^- • C₄H₈O₂)

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

References

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Notes

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

Wiberg, Crocker, et al., 1991
Wiberg, K.B.; Crocker, L.S.; Morgan, K.M., Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups, J. Am. Chem. Soc., 1991, 113, 3447-3450. [all data]

Wiberg and Waldron, 1991
Wiberg, K.B.; Waldron, R.F., Lactones. 2. Enthalpies of hydrolysis, reduction, and formation of the C₄-C₁₃ monocyclic lactones. strain energies and conformations, J. Am. Chem. Soc., 1991, 113, 7697-7705. [all data]

Fenwick, Harrop, et al., 1978
Fenwick, J.O.; Harrop, D.; Head, A.J., Thermodynamic properties of organic oxygen compounds. 46. Enthalpies of formation of ethyl acetate and 1-hexanoix acid, J. Chem. Thermodyn., 1978, 10, 687-690. [all data]

Butwill and Rockenfeller, 1970
Butwill, M.E.; Rockenfeller, J.D., Heats of combustion and formation of ethyl acetate and isopropyl acetate, Thermochim. Acta, 1970, 1, 289-295. [all data]

Stull D.R., 1969
Stull D.R., Jr., The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969. [all data]

Vvedenskii A.A., 1949
Vvedenskii A.A., Thermodynamics of the dehydrogenation reactions of alcohols. The equilibrium 2 C2H5OH = CH3COOC2H5 + 2 H2, Zh. Obshch. Khim., 1949, 19, 1094-1100. [all data]

Dorofeeva O.V., 1997
Dorofeeva O.V., Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]

Parks G.S., 1933
Parks G.S., Thermal data on organic compounds. XI. The heat capacities, entropies and free energies of ten compounds containing oxygen or nitrogen, J. Am. Chem. Soc., 1933, 55, 2733-2740. [all data]

Connett J.E., 1976
Connett J.E., Thermodynamic properties of organic oxygen compounds. XLIV. Vapor heat capacities and enthalpies of vaporization of methyl acetate, ethyl acetate, and propyl acetate, J. Chem. Thermodyn., 1976, 8, 1199-1203. [all data]

Bennewitz K., 1938
Bennewitz K., Molar heats of vapor organic compounds, Z. Phys. Chem. (Leipzig), 1938, B39, 126-144. [all data]

Jatkar S.K.K., 1939
Jatkar S.K.K., Supersonic velocity in gases and vapors. VI. Specific heats of the vapors of alcohols and ethyl acetate, J. Indian Inst. Sci., 1939, A22, 39-58. [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]

Decouzon, Gal, et al., 1996
Decouzon, M.; Gal, J.E.; Herreros, M.; Marai, P.C.; Murrell, J.; Todd, J.F.J., On the Use of the Kinetic Method for the Determination of Proton Affinities by Fourier-Transfrom Ion Cyclotron Resonance Mass Spectrometry, Rapid. Comm. Mass Spectrom., 1996, 10, 242. [all data]

Fraser-Monteiro, Fraser-Monteiro, et al., 1982
Fraser-Monteiro, L.; Fraser-Monteiro, M.L.; Butler, J.J.; Baer, T., Thermochemistry and dissociation dynamics of state-selected C₄H₈O₂⁺ ions. 3. Ethyl acetate, J. Phys. Chem., 1982, 86, 752. [all data]

Jalonen, Tedder, et al., 1980
Jalonen, J.; Tedder, J.M.; Nidaud, P.H., Charge-exchange mass spectra of ethyl acetate, methyl proprionate and propyl formate, J. Chem. Soc. Faraday Trans. 2, 1980, 76, 1450. [all data]

Holmes and Lossing, 1980
Holmes, J.L.; Lossing, F.P., Gas-phase heats of formation of keto and enol ions of carbonyl compounds., J. Am. Chem. Soc., 1980, 102, 1591. [all data]

Benoit, Harrison, et al., 1977
Benoit, F.M.; Harrison, A.G.; Lossing, F.P., Hydrogen migrations in mass spectrometry III-Energetics of formation of [R'CO₂H₂]⁺ in the mass spectra of R'CO₂R, Org. Mass Spectrom., 1977, 12, 78. [all data]

Sweigart and Turner, 1972
Sweigart, D.A.; Turner, D.W., Lone pair orbitals and their interactions studied by photoelectron spectroscopy. I. Carboxylic acids and their derivatives, J. Am. Chem. Soc., 1972, 94, 5592. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

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

Jones, Modelli, et al., 1994
Jones, D.; Modelli, A.; Olivato, P.R.; DalColle, M.; dePalo, M.; Distefano, G., Ab initio and electron spectroscopy study of carbonyl derivatives, J. Chem. Soc. Perkin Trans. 2, 1994, 1994, 1651. [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]

Brion and Dunning, 1963
Brion, C.E.; Dunning, W.J., Electron impact studies of simple carboxylic esters, J. Chem. Soc. Faraday Trans., 1963, 59, 647. [all data]

Friedland and Strakna, 1956
Friedland, S.S.; Strakna, R.E., Appearance potential studies. I, J. Phys. Chem., 1956, 60, 815. [all data]

Holmes, Lossing, et al., 1991
Holmes, J.L.; Lossing, F.P.; Mayer, P.M., Heats of formation of oxygen-containing organic free radicals from appearance energy measurements, J. Am. Chem. Soc., 1991, 113, 9723. [all data]

Godbole and Kebarle, 1962
Godbole, E.W.; Kebarle, P., Ionization and dissociation of deuterated ethyl and isopropyl acetates and ethyl formate under electron impact, J. Chem. Soc. Faraday Trans., 1962, 58, 1897. [all data]

Tsuda and Hamill, 1966
Tsuda, S.; Hamill, W.H., Ionization efficiency measurements by the retarding potential difference method, Advan. Mass Spectrom., 1966, 3, 249. [all data]

Munson and Franklin, 1964
Munson, M.S.B.; Franklin, J.L., Energetics of some gaseous oxygenated organic ions, J. Phys. Chem., 1964, 68, 3191. [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]

Harrison and Jones, 1965
Harrison, A.G.; Jones, E.G., Rearrangement reactions following electron impact on ethyl and isopropyl esters, Can. J. Chem., 1965, 43, 960. [all data]

Holmes, Burgers, et al., 1981
Holmes, J.L.; Burgers, P.C.; Terlouw, J.K., Water elimination from the keto and enol tautomers of ionised ethylacetate, Can. J. Chem., 1981, 59, 1805. [all data]

Bernecker and Long, 1961
Bernecker, R.R.; Long, F., Some organic positive ions and their parent radicals and molecules, J. Phys. Chem., 1961, 65, 1565. [all data]

Haas, Giblin, et al., 1998
Haas, G.W.; Giblin, D.E.; Gross, M.L., The Mechanism and Thermodynamics of Transesterification of Acetate-Ester Enolates in the Gas Phase, Int. J. Mass Spectrom. Ion Proc., 1998, 172, 1-2, 25, https://doi.org/10.1016/S0168-1176(97)83245-4 . [all data]

Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Mazunov, V.A., Determination of electron affinity of carbonyl radicals by means of negative ion mass spectrometry, Rapid Commun. Mass Spectrom., 1999, 13, 12, 1104-1108, https://doi.org/10.1002/(SICI)1097-0231(19990630)13:12<1104::AID-RCM619>3.0.CO;2-C . [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]

Stone and Splinter, 1984
Stone, J.A.; Splinter, D.E., A high-pressure mass spectrometric study of the binding of (CH₃)₃Sn⁺ to lewis bases in the gas phase, Int. J. Mass Spectrom. Ion Processes, 1984, 59, 169. [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]

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]

Notes

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), 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
  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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