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Ethyl Acetate

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Gas phase ion energetics data

Go To: Top, 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)

Quantity Value Units Method Reference Comment
IE (evaluated)10.01 ± 0.05eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)199.7kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity192.3kcal/molN/AHunter and Lias, 1998HL

Gas basicity at 298K

Gas basicity (review) (kcal/mol) Reference Comment
191.2 ± 0.05Decouzon, Gal, et al., 1996T = 338K; MM

Ionization energy determinations

IE (eV) Method Reference Comment
10.01 ± 0.05PIPECOFraser-Monteiro, Fraser-Monteiro, et al., 1982LBLHLM
10.0 ± 0.1CEMSJalonen, Tedder, et al., 1980LLK
10.16EIHolmes and Lossing, 1980LLK
9.90 ± 0.05PEBenoit, Harrison, et al., 1977LLK
10.24PESweigart and Turner, 1972LLK
10.11 ± 0.02PIWatanabe, Nakayama, et al., 1962RDSH
10.09 ± 0.02PIWatanabe, 1957RDSH
10.45PEJones, Modelli, et al., 1994Vertical value; LL
9.90PEBenoit and Harrison, 1977Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH3+13.94 ± 0.08?EIBrion and Dunning, 1963RDSH
C2H3+15.32 ± 0.20?EIFriedland and Strakna, 1956RDSH
C2H3O+11.0 ± 0.15C2H5OPIPECOFraser-Monteiro, Fraser-Monteiro, et al., 1982T = 298K; LBLHLM
C2H3O+11.7 ± 0.3C2H5OCEMSJalonen, Tedder, et al., 1980LLK
C2H3O+11.75 ± 0.07C2H5OEIBrion and Dunning, 1963RDSH
C2H3O2+11.74C2H5EIHolmes, Lossing, et al., 1991LL
C2H4O2+11.2 ± 0.1C2H4EIGodbole and Kebarle, 1962RDSH
C2H5+11.3 ± 0.1C2H3O2PIPECOFraser-Monteiro, Fraser-Monteiro, et al., 1982T = 298K; LBLHLM
C2H5+11.7 ± 0.3CH3COOCEMSJalonen, Tedder, et al., 1980LLK
C2H5+12.1?EITsuda and Hamill, 1966RDSH
C2H5O+10.7 ± 0.1C2H3OPIPECOFraser-Monteiro, Fraser-Monteiro, et al., 1982T = 298K; LBLHLM
C2H5O+10.7 ± 0.2CH3COCEMSJalonen, Tedder, et al., 1980LLK
C2H5O+10.8 ± 0.1CH3COEIMunson and Franklin, 1964RDSH
C2H5O2+10.62 ± 0.05C2H3EIHolmes and Lossing, 1984LBLHLM
C2H5O2+10.67 ± 0.08C2H3PIPECOFraser-Monteiro, Fraser-Monteiro, et al., 1982T = 298K; LBLHLM
C2H5O2+11.0 ± 0.1C2H3CEMSJalonen, Tedder, et al., 1980LLK
C2H5O2+10.6 ± 0.1C2H3EIBenoit, Harrison, et al., 1977LLK
C2H5O2+10.8 ± 0.1?EIHarrison and Jones, 1965RDSH
C3H5O2+10.6 ± 0.1CH3PIPECOFraser-Monteiro, Fraser-Monteiro, et al., 1982T = 298K; LBLHLM
C3H5O2+11.0 ± 0.1CH3EIGodbole and Kebarle, 1962RDSH
C4H6O+10.3 ± 0.1H2OPIPECOFraser-Monteiro, Fraser-Monteiro, et al., 1982T = 298K; LBLHLM
C4H6O+10.32 ± 0.05H2OEIHolmes, Burgers, et al., 1981LLK
C4H6O+10.45H2OEIBernecker and Long, 1961RDSH

De-protonation reactions

C4H7O2- + Hydrogen cation = Ethyl Acetate

By formula: C4H7O2- + H+ = C4H8O2

Quantity Value Units Method Reference Comment
Deltar371.7 ± 4.1kcal/molG+TSHaas, Giblin, et al., 1998gas phase; From transesterification equilibria; B
Deltar368.9 ± 1.2kcal/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Deltar365.0 ± 4.0kcal/molIMREHaas, Giblin, et al., 1998gas phase; From transesterification equilibria; B

References

Go To: Top, 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.

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]


Notes

Go To: Top, Gas phase ion energetics data, References