Acetic acid, methyl ester

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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:
B - John E. Bartmess
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 C3H6O2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)10.25 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)196.4kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity189.0kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
10.2PECannington and Ham, 1985LBLHLM
10.25PITraeger, McLouglin, et al., 1982LBLHLM
10.25 ± 0.05PEBenoit, Harrison, et al., 1977LLK
10.33PESweigart and Turner, 1972LLK
10.27 ± 0.02PIWatanabe, Nakayama, et al., 1962RDSH
10.5PECannington and Ham, 1985Vertical value; LBLHLM
10.25PEBenoit and Harrison, 1977Vertical value; LLK
11.0PERao, 1975Vertical value; LLK
10.59PESustmann and Trill, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CHO+13.95 ± 0.08?EIBrion and Dunning, 1963RDSH
CH2+20.8?EIKing and Long, 1958RDSH
CH3+13.07 ± 0.10?EIBrion and Dunning, 1963RDSH
CH3O+12.52 ± 0.10?EIBrion and Dunning, 1963RDSH
C2H2O+11.81 ± 0.15?EIFriedland and Strakna, 1956RDSH
C2H3O+11.05CH3OPITraeger, McLouglin, et al., 1982LBLHLM
C2H3O+10.9 ± 0.1CH3OEIBurgers and Holmes, 1982LBLHLM
C2H3O+10.94?EIHolmes and Lossing, 1979LLK
C2H3O+11.37 ± 0.05CH3OEIHaney and Franklin, 1969RDSH
C2H3O2+11.32 ± 0.05CH3EIBlanchette, Holmes, et al., 1986LBLHLM
C2H3O2+12.35 ± 0.03CH3EIBriggs and Shannon, 1969RDSH

De-protonation reactions

C3H5O2- + Hydrogen cation = Acetic acid, methyl ester

By formula: C3H5O2- + H+ = C3H6O2

Quantity Value Units Method Reference Comment
Δr371.8 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr371.8 ± 3.7kcal/molD-EAZimmerman, Reed, et al., 1977gas phase; B
Δr375.9 ± 3.5kcal/molEIAEPariat and Allan, 1991gas phase; From CH3CO2Me; B
Quantity Value Units Method Reference Comment
Δr365.1 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B


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, . [all data]

Cannington and Ham, 1985
Cannington, P.H.; Ham, N.S., He(II) photoelectron spectra of esters, J. Electron Spectrosc. Relat. Phenom., 1985, 36, 203. [all data]

Traeger, McLouglin, et al., 1982
Traeger, J.C.; McLouglin, R.G.; Nicholson, A.J.C., Heat of formation for acetyl cation in the gas phase, J. Am. Chem. Soc., 1982, 104, 5318. [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]

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]

Rao, 1975
Rao, C.N.R., Lone-pair ionization bands of chromophores in the photoelectron spectra of organic molecules, Indian J. Chem., 1975, 13, 950. [all data]

Sustmann and Trill, 1972
Sustmann, R.; Trill, H., Photoelektronenspektroskopische Bestimmung von Substituenten-Effekten. II. α,β-ungesattigte Carbonester, Tetrahedron Lett., 1972, 42, 4271. [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]

King and Long, 1958
King, A.B.; Long, F.A., Mass spectra of some simple esters and their interpretation by quasi-equilibrium theory, J. Chem. Phys., 1958, 29, 374. [all data]

Friedland and Strakna, 1956
Friedland, S.S.; Strakna, R.E., Appearance potential studies. I, J. Phys. Chem., 1956, 60, 815. [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 and Lossing, 1979
Holmes, J.L.; Lossing, F.P., Keto and enol forms of methyl acetate molecular ions, their stability and interconvertibility prior to fragmentation in the gas phase, Org. Mass Spectrom., 1979, 14, 512. [all data]

Haney and Franklin, 1969
Haney, M.A.; Franklin, J.L., Excess energies in mass spectra of some oxygen-containing organic compounds, J. Chem. Soc. Faraday Trans., 1969, 65, 1794. [all data]

Blanchette, Holmes, et al., 1986
Blanchette, M.C.; Holmes, J.L.; Hop, C.E.C.A.; Lossing, F.P.; Postma, R.; Ruttink, P.J.A.; Terlouw, J.K., Theory and experiment in concert; the CH3O-C=O+ ion and its isomers, J. Am. Chem. Soc., 1986, 108, 7589. [all data]

Briggs and Shannon, 1969
Briggs, P.R.; Shannon, T.W., The heat of formation of the methoxycarbonyl ion, J. Am. Chem. Soc., 1969, 91, 4307. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Zimmerman, Reed, et al., 1977
Zimmerman, A.H.; Reed, K.J.; Brauman, J.I., Photodetachment of electrons from enolate anions. Gas phase electron affinities of enolate radicals, J. Am. Chem. Soc., 1977, 99, 7203. [all data]

Pariat and Allan, 1991
Pariat, Y.; Allan, M., Dissociative Attachment to Methyl Acetate: Evidence for Ion/Molecule Complexes as Intermediates, Int. J. Mass Spectrom. Ion Proc., 1991, 103, 2-3, 181, . [all data]


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