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Acetic acid

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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
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
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C2H4O2+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)10.65 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)187.3kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity179.9kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
10.63PITraeger, McLouglin, et al., 1982LBLHLM
10.66EIHolmes, Fingas, et al., 1981LLK
10.66 ± 0.05EIHolmes and Lossing, 1980LLK
10.66EIHolmes and Lossing, 1980, 2LLK
10.66 ± 0.05PIAkopyan and Villem, 1976LLK
10.664 ± 0.003PIWatanabe, Yokoyama, et al., 1974LLK
10.644 ± 0.002PIKnowles and Nicholson, 1974LLK
10.65PEWatanabe, Yokoyama, et al., 1973LLK
10.69 ± 0.03PEThomas, 1972LLK
10.70PESweigart and Turner, 1972LLK
10.37 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
10.38 ± 0.03PIVilesov, 1960RDSH
10.35 ± 0.03PIWatanabe, 1957RDSH
10.9PEVon Niessen, Bieri, et al., 1980Vertical value; LLK
10.84PECarnovale, Gan, et al., 1980Vertical value; LLK
10.63PEBenoit and Harrison, 1977Vertical value; LLK
11.5PERao, 1975Vertical value; LLK
10.87PEKimura, Katsumata, et al., 1975Vertical value; LLK
10.8PEGreen and Hayes, 1975Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C+22.0 ± 0.5H2+HCOOHEIStepanov, Perov, et al., 1988LL
CHO2+12.27 ± 0.05CH3EIHaney and Franklin, 1969RDSH
CHO2+12.9 ± 0.1CH3EIShigorin, Filyugina, et al., 1966RDSH
CH3+14.0 ± 0.15?EIHaney and Franklin, 1969RDSH
CH3O+12.05 ± 0.10CHOEISelim and Helal, 1981LLK
CO+15.3 ± 0.1CH3OHEIShigorin, Filyugina, et al., 1966RDSH
C2H3O+11.54OHPITraeger, McLouglin, et al., 1982LBLHLM
C2H3O+11.75OHEIHaney and Franklin, 1969RDSH
C2H3O+11.4 ± 0.15OHEIShigorin, Filyugina, et al., 1966RDSH
OH+15.1?EIMajer, Patrick, et al., 1961RDSH

De-protonation reactions

MeCO2 anion + Hydrogen cation = Acetic acid

By formula: C2H3O2- + H+ = C2H4O2

Quantity Value Units Method Reference Comment
Deltar348.2 ± 1.4kcal/molCIDCAngel and Ervin, 2006gas phase; B
Deltar348.1 ± 2.2kcal/molG+TSTaft and Topsom, 1987gas phase; B
Deltar348.6 ± 2.1kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Deltar348.7 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar343.20 ± 0.70kcal/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Deltar341.1 ± 2.0kcal/molIMRETaft and Topsom, 1987gas phase; B
Deltar341.5 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B
Deltar341.7 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

C2H3O2- + Hydrogen cation = Acetic acid

By formula: C2H3O2- + H+ = C2H4O2

Quantity Value Units Method Reference Comment
Deltar368.0 ± 3.1kcal/molG+TSGrabowski and Cheng, 1989gas phase; B
Deltar367.8 ± 4.6kcal/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase; B
Quantity Value Units Method Reference Comment
Deltar361.2 ± 3.0kcal/molIMRBGrabowski and Cheng, 1989gas phase; 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]

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]

Holmes, Fingas, et al., 1981
Holmes, J.L.; Fingas, M.; Lossing, F.P., Towards a general scheme for estimating the heats of formation of organic ions in the gas phase. Part I. Odd-electron cations, Can. J. Chem., 1981, 59, 80. [all data]

Holmes and Lossing, 1980
Holmes, J.L.; Lossing, F.P., Thermochemistry and unimolecular reactions of ionized acetic acid and its enol in the gas phase., J. Am. Chem. Soc., 1980, 102, 3732. [all data]

Holmes and Lossing, 1980, 2
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]

Akopyan and Villem, 1976
Akopyan, M.E.; Villem, Ya.Ya., Ion-molecule reactions in the photoionization of formic and acetic acid vapors, High Energy Chem., 1976, 10, 24. [all data]

Watanabe, Yokoyama, et al., 1974
Watanabe, I.; Yokoyama, Y.; Ikeda, S., Vibrational structures in the He(I) photoelectron spectra of carboxylic acids, Bull. Chem. Soc. Jpn., 1974, 47, 627. [all data]

Knowles and Nicholson, 1974
Knowles, D.J.; Nicholson, A.J.C., Ionization energies of formic and acetic acid monomers, J. Chem. Phys., 1974, 60, 1180. [all data]

Watanabe, Yokoyama, et al., 1973
Watanabe, I.; Yokoyama, Y.; Ikeda, S., Lone pair ionization potentials of carboxylic acids determined by He(I) photoelectron spectroscopy, Bull. Chem. Soc. Jpn., 1973, 46, 1959. [all data]

Thomas, 1972
Thomas, R.K., Photoelectron spectroscopy of hydrogen-bonded systems: spectra of monomers, dimers and mixed complexes of carboxylic acides, Proc. R. Soc. London A:, 1972, 331, 249. [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]

Vilesov, 1960
Vilesov, F.I., The photoionization of vapors of compounds whose molecules contain carbonyl groups, Dokl. Phys. Chem., 1960, 132, 521, In original 1332. [all data]

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

Von Niessen, Bieri, et al., 1980
Von Niessen, W.; Bieri, G.; Asbrink, L., 30.4 nm He(II) photoelectron spectra of organic molecules. Part III. Oxo-compounds (C,H,O), J. Electron Spectrosc. Relat. Phenom., 1980, 21, 175. [all data]

Carnovale, Gan, et al., 1980
Carnovale, F.; Gan, T.H.; Peel, J.B., Photoelectron spectroscopic studies of the monomers and dimers of acetic and trifluoracetic acids, J. Electron Spectrosc. Relat. Phenom., 1980, 20, 53. [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]

Kimura, Katsumata, et al., 1975
Kimura, K.; Katsumata, S.; Yamazaki, T.; Wakabayashi, H., UV photoelectron spectra and sum rule consideration; out-of-plane orbitals of unsaturated compounds with planar-skeleton structure, J. Electron Spectrosc. Relat. Phenom., 1975, 6, 41. [all data]

Green and Hayes, 1975
Green, J.C.; Hayes, A.J., Ionization energies of an Mo-Mo quadruple bond; a He(I) photoelectron study of some molybdenum-dycarboxylate dimers, Chem. Phys. Lett., 1975, 31, 306. [all data]

Stepanov, Perov, et al., 1988
Stepanov, A.N.; Perov, A.A.; Kabanov, S.P.; Simonov, A.P., Formation of long-lived, highly excited atoms during dissociative excitation of CH3CN, CH3CH2OH, CH3COOH, HCOOH, and C4H4S molecules on electron impact, Russ. J. Phys. Chem., 1988, 22, 81. [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]

Shigorin, Filyugina, et al., 1966
Shigorin, D.N.; Filyugina, A.D.; Potapov, V.K., Ionization and dissociation of molecules of acetaldehyde, acetone, and acetic acid on electron impact, Teor. i Eksperim. Khim., 1966, 2, 554, In original 417. [all data]

Selim and Helal, 1981
Selim, E.T.M.; Helal, A.I., Heat of formation of CH2=OH+ fragment ion, Indian J. Pure Appl. Phys., 1981, 19, 977. [all data]

Majer, Patrick, et al., 1961
Majer, J.R.; Patrick, C.R.; Robb, J.C., Appearance potentials of the acetyl radical-ion, J. Chem. Soc. Faraday Trans., 1961, 57, 14. [all data]

Angel and Ervin, 2006
Angel, L.A.; Ervin, K.M., Gas-phase acidities and O-H bond dissociation enthalpies of phenol, 3-methylphenol, 2,4,6-trimethylphenol, and ethanoic acid, J. Phys. Chem. A, 2006, 110, 35, 10392-10403, https://doi.org/10.1021/jp0627426 . [all data]

Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D., The Nature and Analysis of Substituent Effects, Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [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]

Grabowski and Cheng, 1989
Grabowski, J.J.; Cheng, X., Gas-Phase Formation of the Enolate Monoanion of Acetic Acid by Proton Abstraction, J. Am. Chem. Soc., 1989, 111, 8, 3106, https://doi.org/10.1021/ja00190a078 . [all data]


Notes

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