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Acetic acid, protonated


Reaction thermochemistry data

Go To: Top, Ion clustering data, References, Notes

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. 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

C2H5O+ + Acetic acid = (C2H5O+ bullet Acetic acid)

By formula: C2H5O+ + C2H4O2 = (C2H5O+ bullet C2H4O2)

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

Quantity Value Units Method Reference Comment
Deltar28.1kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase
Deltar29.5kcal/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Deltar28.3cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase
Deltar27.9cal/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Deltar21.2kcal/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986

C2H5O+ + Ethanol = (C2H5O+ bullet Ethanol)

By formula: C2H5O+ + C2H6O = (C2H5O+ bullet C2H6O)

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

Quantity Value Units Method Reference Comment
Deltar29.5kcal/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Deltar26.0cal/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Deltar21.7kcal/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986

C2H5O+ + Acetaldehyde = (C2H5O+ bullet Acetaldehyde)

By formula: C2H5O+ + C2H4O = (C2H5O+ bullet C2H4O)

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

Quantity Value Units Method Reference Comment
Deltar29.0kcal/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Deltar26.2cal/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Deltar21.2kcal/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986

(C2H5O+ bullet 3Acetic acid) + Acetic acid = (C2H5O+ bullet 4Acetic acid)

By formula: (C2H5O+ bullet 3C2H4O2) + C2H4O2 = (C2H5O+ bullet 4C2H4O2)

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

Quantity Value Units Method Reference Comment
Deltar12.kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Deltar25.cal/mol*KN/AMeot-Ner (Mautner), 1992gas phase; Entropy change calculated or estimated

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
6.2245.PHPMSMeot-Ner (Mautner), 1992gas phase; Entropy change calculated or estimated

C2H5O+ + Water = (C2H5O+ bullet Water)

By formula: C2H5O+ + H2O = (C2H5O+ bullet H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Deltar20.1kcal/molPHPMSMeot-Ner (Mautner), 1984gas phase
Deltar21.9kcal/molHPMSDavidson, Sunner J., et al., 1979gas phase
Quantity Value Units Method Reference Comment
Deltar21.0cal/mol*KPHPMSMeot-Ner (Mautner), 1984gas phase

(C2H5O+ bullet 2Acetic acid) + Acetic acid = (C2H5O+ bullet 3Acetic acid)

By formula: (C2H5O+ bullet 2C2H4O2) + C2H4O2 = (C2H5O+ bullet 3C2H4O2)

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

Quantity Value Units Method Reference Comment
Deltar13.1kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase
Quantity Value Units Method Reference Comment
Deltar22.4cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase

(C2H5O+ bullet Acetic acid) + Acetic acid = (C2H5O+ bullet 2Acetic acid)

By formula: (C2H5O+ bullet C2H4O2) + C2H4O2 = (C2H5O+ bullet 2C2H4O2)

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

Quantity Value Units Method Reference Comment
Deltar18.5kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase
Quantity Value Units Method Reference Comment
Deltar24.5cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase

(C2H5O+ bullet 2Water) + Water = (C2H5O+ bullet 3Water)

By formula: (C2H5O+ bullet 2H2O) + H2O = (C2H5O+ bullet 3H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Deltar12.9kcal/molPHPMSMeot-Ner (Mautner), 1984gas phase
Quantity Value Units Method Reference Comment
Deltar23.2cal/mol*KPHPMSMeot-Ner (Mautner), 1984gas phase

(C2H5O+ bullet 3Water) + Water = (C2H5O+ bullet 4Water)

By formula: (C2H5O+ bullet 3H2O) + H2O = (C2H5O+ bullet 4H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Deltar10.8kcal/molPHPMSMeot-Ner (Mautner), 1984gas phase
Quantity Value Units Method Reference Comment
Deltar20.4cal/mol*KPHPMSMeot-Ner (Mautner), 1984gas phase

(C2H5O+ bullet Water) + Water = (C2H5O+ bullet 2Water)

By formula: (C2H5O+ bullet H2O) + H2O = (C2H5O+ bullet 2H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Deltar17.8kcal/molPHPMSMeot-Ner (Mautner), 1984gas phase
Quantity Value Units Method Reference Comment
Deltar26.4cal/mol*KPHPMSMeot-Ner (Mautner), 1984gas phase

Ion clustering data

Go To: Top, Reaction thermochemistry data, References, Notes

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

C2H5O+ + Acetaldehyde = (C2H5O+ bullet Acetaldehyde)

By formula: C2H5O+ + C2H4O = (C2H5O+ bullet C2H4O)

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

Quantity Value Units Method Reference Comment
Deltar29.0kcal/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Deltar26.2cal/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Deltar21.2kcal/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986

C2H5O+ + Acetic acid = (C2H5O+ bullet Acetic acid)

By formula: C2H5O+ + C2H4O2 = (C2H5O+ bullet C2H4O2)

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

Quantity Value Units Method Reference Comment
Deltar28.1kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase
Deltar29.5kcal/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Deltar28.3cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase
Deltar27.9cal/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Deltar21.2kcal/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986

(C2H5O+ bullet Acetic acid) + Acetic acid = (C2H5O+ bullet 2Acetic acid)

By formula: (C2H5O+ bullet C2H4O2) + C2H4O2 = (C2H5O+ bullet 2C2H4O2)

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

Quantity Value Units Method Reference Comment
Deltar18.5kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase
Quantity Value Units Method Reference Comment
Deltar24.5cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase

(C2H5O+ bullet 2Acetic acid) + Acetic acid = (C2H5O+ bullet 3Acetic acid)

By formula: (C2H5O+ bullet 2C2H4O2) + C2H4O2 = (C2H5O+ bullet 3C2H4O2)

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

Quantity Value Units Method Reference Comment
Deltar13.1kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase
Quantity Value Units Method Reference Comment
Deltar22.4cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase

(C2H5O+ bullet 3Acetic acid) + Acetic acid = (C2H5O+ bullet 4Acetic acid)

By formula: (C2H5O+ bullet 3C2H4O2) + C2H4O2 = (C2H5O+ bullet 4C2H4O2)

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

Quantity Value Units Method Reference Comment
Deltar12.kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; Entropy change calculated or estimated
Quantity Value Units Method Reference Comment
Deltar25.cal/mol*KN/AMeot-Ner (Mautner), 1992gas phase; Entropy change calculated or estimated

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
6.2245.PHPMSMeot-Ner (Mautner), 1992gas phase; Entropy change calculated or estimated

C2H5O+ + Ethanol = (C2H5O+ bullet Ethanol)

By formula: C2H5O+ + C2H6O = (C2H5O+ bullet C2H6O)

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

Quantity Value Units Method Reference Comment
Deltar29.5kcal/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Deltar26.0cal/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986
Quantity Value Units Method Reference Comment
Deltar21.7kcal/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986

C2H5O+ + Water = (C2H5O+ bullet Water)

By formula: C2H5O+ + H2O = (C2H5O+ bullet H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Deltar20.1kcal/molPHPMSMeot-Ner (Mautner), 1984gas phase
Deltar21.9kcal/molHPMSDavidson, Sunner J., et al., 1979gas phase
Quantity Value Units Method Reference Comment
Deltar21.0cal/mol*KPHPMSMeot-Ner (Mautner), 1984gas phase

(C2H5O+ bullet Water) + Water = (C2H5O+ bullet 2Water)

By formula: (C2H5O+ bullet H2O) + H2O = (C2H5O+ bullet 2H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Deltar17.8kcal/molPHPMSMeot-Ner (Mautner), 1984gas phase
Quantity Value Units Method Reference Comment
Deltar26.4cal/mol*KPHPMSMeot-Ner (Mautner), 1984gas phase

(C2H5O+ bullet 2Water) + Water = (C2H5O+ bullet 3Water)

By formula: (C2H5O+ bullet 2H2O) + H2O = (C2H5O+ bullet 3H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Deltar12.9kcal/molPHPMSMeot-Ner (Mautner), 1984gas phase
Quantity Value Units Method Reference Comment
Deltar23.2cal/mol*KPHPMSMeot-Ner (Mautner), 1984gas phase

(C2H5O+ bullet 3Water) + Water = (C2H5O+ bullet 4Water)

By formula: (C2H5O+ bullet 3H2O) + H2O = (C2H5O+ bullet 4H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Deltar10.8kcal/molPHPMSMeot-Ner (Mautner), 1984gas phase
Quantity Value Units Method Reference Comment
Deltar20.4cal/mol*KPHPMSMeot-Ner (Mautner), 1984gas phase

References

Go To: Top, Reaction thermochemistry data, Ion clustering data, Notes

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

Meot-Ner (Mautner), 1992
Meot-Ner (Mautner), M., Intermolecular Forces in Organic Clusters, J. Am. Chem. Soc., 1992, 114, 9, 3312, https://doi.org/10.1021/ja00035a024 . [all data]

Larson and McMahon, 1982
Larson, J.W.; McMahon, T.B., Formation, Thermochemistry, and Relative Stabilities of Proton - Bound dimers of Oxygen n - Donor Bases from Ion Cyclotron Resonance Solvent - Exchange Equilibria Measurements, J. Am. Chem. Soc., 1982, 104, 23, 6255, https://doi.org/10.1021/ja00387a016 . [all data]

Grimsrud and Kebarle, 1973
Grimsrud, E.P.; Kebarle, P., Gas Phase Ion Equilibria Studies of the Solvation of the Hydrogen Ion by Methanol, Dimethyl Ether and Water. Effect of Hydrogen Bonding, J. Am. Chem. Soc., 1973, 95, 24, 7939, https://doi.org/10.1021/ja00805a002 . [all data]

Lias, Liebman, et al., 1984
Lias, S.G.; Liebman, J.F.; Levin, R.D., Evaluated gas phase basicities and proton affinities of molecules heats of formation of protonated molecules, J. Phys. Chem. Ref. Data, 1984, 13, 695. [all data]

Keesee and Castleman, 1986
Keesee, R.G.; Castleman, A.W., Jr., Thermochemical data on Ggs-phase ion-molecule association and clustering reactions, J. Phys. Chem. Ref. Data, 1986, 15, 1011. [all data]

Meot-Ner (Mautner), 1984
Meot-Ner (Mautner), M., The Ionic Hydrogen Bond and Ion Solvation. 2. Hydration of Onium Ions by 1 - 7 H2O Molecules. Relations Between Monomolecular, Specific and Bulk Hydration, J. Am. Chem. Soc., 1984, 106, 5, 1265, https://doi.org/10.1021/ja00317a016 . [all data]

Davidson, Sunner J., et al., 1979
Davidson, W.R.; Sunner J.; Kebarle, P., Hydrogen Bonding of Water to Onium Ions. Hydration of Substituted Pyridinium Ions and Related Systems, J. Am. Chem. Soc., 1979, 101, 7, 1675, https://doi.org/10.1021/ja00501a005 . [all data]


Notes

Go To: Top, Reaction thermochemistry data, Ion clustering data, References