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Acetic acid, methyl ester

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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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar

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

C3H7O2+ + Acetic acid, methyl ester = (C3H7O2+ bullet Acetic acid, methyl ester)

By formula: C3H7O2+ + C3H6O2 = (C3H7O2+ bullet C3H6O2)

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

Quantity Value Units Method Reference Comment
Deltar29.1kcal/molPHPMSSzulejko and McMahon, 1991gas phase; M
Deltar29.7kcal/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; M
Quantity Value Units Method Reference Comment
Deltar33.8cal/mol*KPHPMSSzulejko and McMahon, 1991gas phase; M
Deltar30.9cal/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; M
Quantity Value Units Method Reference Comment
Deltar20.5kcal/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; M

C3H5O2- + Hydrogen cation = Acetic acid, methyl ester

By formula: C3H5O2- + H+ = C3H6O2

Quantity Value Units Method Reference Comment
Deltar371.8 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar371.8 ± 3.7kcal/molD-EAZimmerman, Reed, et al., 1977gas phase; B
Deltar375.9 ± 3.5kcal/molEIAEPariat and Allan, 1991gas phase; From CH3CO2Me; B
Quantity Value Units Method Reference Comment
Deltar365.1 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

C3H9Sn+ + Acetic acid, methyl ester = (C3H9Sn+ bullet Acetic acid, methyl ester)

By formula: C3H9Sn+ + C3H6O2 = (C3H9Sn+ bullet C3H6O2)

Quantity Value Units Method Reference Comment
Deltar38.4kcal/molPHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar32.6cal/mol*KN/AStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
21.3525.PHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

Ethane, 1,1,1-trimethoxy- + Water = 2Methyl Alcohol + Acetic acid, methyl ester

By formula: C5H12O3 + H2O = 2CH4O + C3H6O2

Quantity Value Units Method Reference Comment
Deltar-6.426 ± 0.007kcal/molCmWiberg, Martin, et al., 1985liquid phase; solvent: Aqueous dioxane; ALS
Deltar-6.4641 ± 0.0072kcal/molCmWiberg and Squires, 1979liquid phase; solvent: Water; Hydrolysis; ALS

CH6N+ + Acetic acid, methyl ester = (CH6N+ bullet Acetic acid, methyl ester)

By formula: CH6N+ + C3H6O2 = (CH6N+ bullet C3H6O2)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity Value Units Method Reference Comment
Deltar23.5kcal/molPHPMSMeot-Ner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar24.8cal/mol*KPHPMSMeot-Ner, 1984gas phase; M

Nitric oxide anion + Acetic acid, methyl ester = (Nitric oxide anion bullet Acetic acid, methyl ester)

By formula: NO- + C3H6O2 = (NO- bullet C3H6O2)

Quantity Value Units Method Reference Comment
Deltar39.8kcal/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

Lithium ion (1+) + Acetic acid, methyl ester = (Lithium ion (1+) bullet Acetic acid, methyl ester)

By formula: Li+ + C3H6O2 = (Li+ bullet C3H6O2)

Quantity Value Units Method Reference Comment
Deltar44.kcal/molICRStaley and Beauchamp, 1975gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 extrapolated; M

Sodium ion (1+) + Acetic acid, methyl ester = (Sodium ion (1+) bullet Acetic acid, methyl ester)

By formula: Na+ + C3H6O2 = (Na+ bullet C3H6O2)

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
23.3298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89; RCD

Water + Acetic acid, methyl ester = Acetic acid + Methyl Alcohol

By formula: H2O + C3H6O2 = C2H4O2 + CH4O

Quantity Value Units Method Reference Comment
Deltar1.05kcal/molCmCoon and Daniels, 1933liquid phase; solvent: in HCl; ALS

Ketene + Methyl Alcohol = Acetic acid, methyl ester

By formula: C2H2O + CH4O = C3H6O2

Quantity Value Units Method Reference Comment
Deltar-36.93kcal/molCmRice and Greenberg, 1934gas phase; ALS

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.

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]

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]

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, https://doi.org/10.1016/0168-1176(91)80088-5 . [all data]

Stone and Splinter, 1984
Stone, J.A.; Splinter, D.E., A high-pressure mass spectrometric study of the binding of (CH3)3Sn+ to lewis bases in the gas phase, Int. J. Mass Spectrom. Ion Processes, 1984, 59, 169. [all data]

Wiberg, Martin, et al., 1985
Wiberg, K.B.; Martin, E.J.; Squires, R.R., Thermochemical studies of carbonyl compounds. 3. Enthalpies of hydrolysis of ortho esters, J. Org. Chem., 1985, 50, 4717-4720. [all data]

Wiberg and Squires, 1979
Wiberg, K.B.; Squires, R.R., A microprocessor-controlled system for precise measurement of temperature changes. Determination of the enthalpies of hydrolysis of some polyoxygenated hydrocarbons, J. Chem. Thermodyn., 1979, 11, 773-786. [all data]

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]

Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L., Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases, J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050 . [all data]

Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P., Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n, J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013 . [all data]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]

Coon and Daniels, 1933
Coon, E.D.; Daniels, F., An isothermal calorimeter for slow reactions, J. Phys. Chem., 1933, 37, 1-12. [all data]

Rice and Greenberg, 1934
Rice, F.O.; Greenberg, J., Ketene. III. Heat of formation and heat of reaction with alcohols, J. Am. Chem. Soc., 1934, 38, 2268-2270. [all data]


Notes

Go To: Top, Reaction thermochemistry data, References