Acetone, protonated

Reaction 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 by: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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Individual Reactions

C3H7O+ + Acetone = (C3H7O+ • Acetone)

By formula: C3H7O+ + C3H6O = (C3H7O+ • C3H6O)

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

Quantity Value Units Method Reference Comment
ΔrH°128.kJ/molPHPMSMeot-Ner (Mautner) and Sieck, 1991gas phase
ΔrH°126.kJ/molPHPMSSzulejko and McMahon, 1991gas phase
ΔrH°124.kJ/molPHPMSHiraoka and Takimoto, 1986gas phase
ΔrH°132.kJ/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
ΔrH°126.kJ/molPHPMSLau, Saluja, et al., 1980gas phase
Quantity Value Units Method Reference Comment
ΔrS°118.J/mol*KPHPMSMeot-Ner (Mautner) and Sieck, 1991gas phase
ΔrS°128.J/mol*KPHPMSSzulejko and McMahon, 1991gas phase
ΔrS°123.J/mol*KPHPMSHiraoka and Takimoto, 1986gas phase
ΔrS°129.J/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
ΔrS°127.J/mol*KPHPMSLau, Saluja, et al., 1980gas phase
Quantity Value Units Method Reference Comment
ΔrG°93.3kJ/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

C3H7O+ + 1,4-Dioxane = (C3H7O+ • 1,4-Dioxane)

By formula: C3H7O+ + C4H8O2 = (C3H7O+ • C4H8O2)

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

Quantity Value Units Method Reference Comment
ΔrH°126.kJ/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
ΔrS°126.J/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
ΔrG°87.9kJ/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

(C3H7O+ • 2Acetone) + Acetone = (C3H7O+ • 3Acetone)

By formula: (C3H7O+ • 2C3H6O) + C3H6O = (C3H7O+ • 3C3H6O)

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

Quantity Value Units Method Reference Comment
ΔrH°36.kJ/molPHPMSHiraoka, Takimoto, et al., 1986gas phase
Quantity Value Units Method Reference Comment
ΔrS°71.1J/mol*KPHPMSHiraoka, Takimoto, et al., 1986gas phase

(C3H7O+ • Acetone) + Acetone = (C3H7O+ • 2Acetone)

By formula: (C3H7O+ • C3H6O) + C3H6O = (C3H7O+ • 2C3H6O)

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

Quantity Value Units Method Reference Comment
ΔrH°51.0kJ/molPHPMSHiraoka, Morise, et al., 1986gas phase
Quantity Value Units Method Reference Comment
ΔrS°96.2J/mol*KPHPMSHiraoka, Morise, et al., 1986gas phase

(C3H7O+ • 2Water) + Water = (C3H7O+ • 3Water)

By formula: (C3H7O+ • 2H2O) + H2O = (C3H7O+ • 3H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
ΔrH°53.1kJ/molPHPMSMeot-Ner (Mautner), 1984gas phase
Quantity Value Units Method Reference Comment
ΔrS°91.6J/mol*KPHPMSMeot-Ner (Mautner), 1984gas phase

(C3H7O+ • 3Water) + Water = (C3H7O+ • 4Water)

By formula: (C3H7O+ • 3H2O) + H2O = (C3H7O+ • 4H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
ΔrH°43.1kJ/molPHPMSMeot-Ner (Mautner), 1984gas phase
Quantity Value Units Method Reference Comment
ΔrS°84.5J/mol*KPHPMSMeot-Ner (Mautner), 1984gas phase

(C3H7O+ • 4Water) + Water = (C3H7O+ • 5Water)

By formula: (C3H7O+ • 4H2O) + H2O = (C3H7O+ • 5H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
ΔrH°43.1kJ/molPHPMSMeot-Ner (Mautner), 1984gas phase
Quantity Value Units Method Reference Comment
ΔrS°98.3J/mol*KPHPMSMeot-Ner (Mautner), 1984gas phase

(C3H7O+ • Water) + Water = (C3H7O+ • 2Water)

By formula: (C3H7O+ • H2O) + H2O = (C3H7O+ • 2H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
ΔrH°56.9kJ/molPHPMSMeot-Ner (Mautner), 1984gas phase
Quantity Value Units Method Reference Comment
ΔrS°97.1J/mol*KPHPMSMeot-Ner (Mautner), 1984gas phase

C3H7O+ + Water = (C3H7O+ • Water)

By formula: C3H7O+ + H2O = (C3H7O+ • H2O)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
ΔrH°85.8kJ/molPHPMSMeot-Ner (Mautner), 1984gas phase
Quantity Value Units Method Reference Comment
ΔrS°109.J/mol*KPHPMSMeot-Ner (Mautner), 1984gas phase

C3H7O+ + Hydrogen cyanide = (C3H7O+ • Hydrogen cyanide)

By formula: C3H7O+ + CHN = (C3H7O+ • CHN)

Quantity Value Units Method Reference Comment
ΔrH°85.4kJ/molPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase
Quantity Value Units Method Reference Comment
ΔrS°98.7J/mol*KPHPMSSpeller and Meot-Ner (Mautner), 1985gas phase

C3H7O+ + Acetonitrile = (C3H7O+ • Acetonitrile)

By formula: C3H7O+ + C2H3N = (C3H7O+ • C2H3N)

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
87.0320.ICRBromilow, Abboud, et al., 1980gas phase; switching reaction,n((CH3)2OH+)(CH3)2O; Grimsrud and Kebarle, 1973

References

Go To: Top, Reaction thermochemistry 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) and Sieck, 1991
Meot-Ner (Mautner), M.; Sieck, L.W., Proton affinity ladders from variable-temperature equilibrium measurements. 1. A reevaluation of the upper proton affinity range, J. Am. Chem. Soc., 1991, 113, 12, 4448, https://doi.org/10.1021/ja00012a012 . [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]

Hiraoka and Takimoto, 1986
Hiraoka, K.; Takimoto, H., Gas-Phase Stabilities of Symmetric Proton-Held Dimer Cations, J. Phys. Chem., 1986, 90, 22, 5910, https://doi.org/10.1021/j100280a090 . [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]

Lau, Saluja, et al., 1980
Lau, Y.K.; Saluja, P.P.S.; Kebarle, P., The Proton in Dimethyl Sulfoxide and Acetone. Results from Gas - Phase Ion Equilibria Involving (Me2SO)nH+ and (Me2CO)nH+, J. Am. Chem. Soc., 1980, 102, 25, 7429, https://doi.org/10.1021/ja00545a004 . [all data]

Hiraoka, Takimoto, et al., 1986
Hiraoka, K.; Takimoto, H.; Morise, K.; Shoda, T.; Nakamura, S., Ion-Molecule Reactions in Gaseous Acetone, Bull. Chem. Soc. Japan, 1986, 59, 7, 2247, https://doi.org/10.1246/bcsj.59.2247 . [all data]

Hiraoka, Morise, et al., 1986
Hiraoka, K.; Morise, K.; Nishijima, T.; Nakamura, S.; Nakazato, M.; Ohkuma, K., Gas Phase Ion Equilibria Studies of Protons and Chloride Ions in Propanol and Acetone, Int. J. Mass Spectrom. Ion Proc., 1986, 68, 1-2, 99, https://doi.org/10.1016/0168-1176(86)87071-9 . [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]

Speller and Meot-Ner (Mautner), 1985
Speller, C.V.; Meot-Ner (Mautner), M., The Ionic Hydrogen Bond and Ion Solvation. 3. Bonds Involving Cyanides. Correlations with Proton Affinites, J. Phys. Chem., 1985, 81, 24, 5217, https://doi.org/10.1021/j100270a020 . [all data]

Bromilow, Abboud, et al., 1980
Bromilow, J.; Abboud, J.L.M.; Lebrilla, C.B.; Taft, R.W.; Scorrano, G.; Lucchini, V., Oxonium Ions. Solvation by Single Acetonitrile Molecules in the Gas Phase and by Bulk Solvents, J. Am. Chem. Soc., 1980, 103, 18, 5448, https://doi.org/10.1021/ja00408a028 . [all data]

Notes

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