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Acetic acid, methyl ester

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Gas phase 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas-410.0kJ/molCcrHall and Baldt, 1971ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
55.78100.Chao J., 1986p=1 bar. Recommended Cp(T) values are in close agreement with those calculated by [ Vay P.-M., 1971]. S(T) values calculated by [ Vay P.-M., 1971] are 4.6-4.8 J/mol*K lower than those of [ Chao J., 1986].; GT
63.27150.
70.02200.
81.56273.15
86.03 ± 0.12298.15
86.37300.
105.31400.
123.40500.
139.25600.
152.84700.
164.47800.
174.46900.
183.061000.
190.471100.
196.871200.
202.391300.
207.181400.
211.341500.

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
92.58335.0Connett J.E., 1976GT
95.46350.0
100.39375.0
105.31400.0
109.98425.0
114.63450.0

Condensed phase 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid-445.89kJ/molCcrHall and Baldt, 1971ALS
Quantity Value Units Method Reference Comment
Deltacliquid-1583.kJ/molCcbSeno, Tsuchiya, et al., 1975Corresponding «DELTA»fliquid = -455.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-1592.2 ± 0.67kJ/molCcrHall and Baldt, 1971Corresponding «DELTA»fliquid = -445.85 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
140.2288.58Okamoto, Oguni, et al., 1992T = 13 to 290 K. Unsmoothed experimental datum.; DH
141.34298.15Pintos, Bravo, et al., 1988DH
140.6298.15Costas and Patterson, 1985T = 283.15, 298.15, 313.15 K.; DH
140.56298.15Costas and Patterson, 1985, 2T = 283.15, 298.15, 313.15 K.; DH
123.7297.Hall and Baldt, 1971DH

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
Deltar122.kJ/molPHPMSSzulejko and McMahon, 1991gas phase; M
Deltar124.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; M
Quantity Value Units Method Reference Comment
Deltar141.J/mol*KPHPMSSzulejko and McMahon, 1991gas phase; M
Deltar129.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; M
Quantity Value Units Method Reference Comment
Deltar85.8kJ/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
Deltar1556. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar1556. ± 15.kJ/molD-EAZimmerman, Reed, et al., 1977gas phase; B
Deltar1573. ± 15.kJ/molEIAEPariat and Allan, 1991gas phase; From CH3CO2Me; B
Quantity Value Units Method Reference Comment
Deltar1528. ± 8.4kJ/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
Deltar161.kJ/molPHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar136.J/mol*KN/AStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
89.1525.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-26.89 ± 0.03kJ/molCmWiberg, Martin, et al., 1985liquid phase; solvent: Aqueous dioxane; ALS
Deltar-27.046 ± 0.030kJ/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
Deltar98.3kJ/molPHPMSMeot-Ner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar104.J/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
Deltar167.kJ/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
Deltar180.kJ/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° (kJ/mol) T (K) Method Reference Comment
97.5298.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
Deltar4.39kJ/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-154.5kJ/molCmRice and Greenberg, 1934gas phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

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

Hall and Baldt, 1971
Hall, H.K., Jr.; Baldt, J.H., Thermochemistry of strained-ring bridgehead nitriles and esters, J. Am. Chem. Soc., 1971, 93, 140-145. [all data]

Chao J., 1986
Chao J., Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties, J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]

Vay P.-M., 1971
Vay P.-M., Tables of thermodynamic functions for gaseous methyl formate and methyl acetate, J. Chim. Phys. Physico-Chim. Biol., 1971, 68, 1757-1758. [all data]

Connett J.E., 1976
Connett J.E., Thermodynamic properties of organic oxygen compounds. XLIV. Vapor heat capacities and enthalpies of vaporization of methyl acetate, ethyl acetate, and propyl acetate, J. Chem. Thermodyn., 1976, 8, 1199-1203. [all data]

Seno, Tsuchiya, et al., 1975
Seno, M.; Tsuchiya, S.; Kise, H.; Asahara, T., Studies on bond character in phosphorus ylides by combustion heat and x-ray photoelectron spectroscopy, Bull. Chem. Soc. Jpn., 1975, 48, 2001-2005. [all data]

Okamoto, Oguni, et al., 1992
Okamoto, N.; Oguni, M.; Suga, H., Low temperature calorimetric study of methyl acetate, Thermochim. Acta, 1992, 202, 215-222. [all data]

Pintos, Bravo, et al., 1988
Pintos, M.; Bravo, R.; Baluja, M.C.; Paz Andrade, M.I.; Roux-Desgranges, G.; Grolier, J.-P.E., Can. J. Chem., 1988, 1179. [all data]

Costas and Patterson, 1985
Costas, M.; Patterson, D., Heat capacities of water + organic-solvent mixtures, J. Chem. Soc., Faraday Trans. 1, 1985, 81, 2381-2398. [all data]

Costas and Patterson, 1985, 2
Costas, M.; Patterson, D., Self-association of alcohols in inert solvents, J. Chem. Soc., Faraday Trans. 1, 1985, 81, 635-654. [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]

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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References