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Ethyl formate

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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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

C3H7O2+ + Ethyl formate = (C3H7O2+ bullet Ethyl formate)

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

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

Quantity Value Units Method Reference Comment
Deltar126.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
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
Deltar87.0kJ/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

C4H9O2+ + Ethyl formate = (C4H9O2+ bullet Ethyl formate)

By formula: C4H9O2+ + C3H6O2 = (C4H9O2+ bullet C3H6O2)

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

Quantity Value Units Method Reference Comment
Deltar128.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
Deltar125.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
Deltar90.4kJ/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

thiophenoxide anion + Ethyl formate = (thiophenoxide anion bullet Ethyl formate)

By formula: C6H5S- + C3H6O2 = (C6H5S- bullet C3H6O2)

Quantity Value Units Method Reference Comment
Deltar83.7kJ/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar107.J/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

Iodide + Ethyl formate = (Iodide bullet Ethyl formate)

By formula: I- + C3H6O2 = (I- bullet C3H6O2)

Quantity Value Units Method Reference Comment
Deltar69.5kJ/molPHPMSCaldwell and Kebarle, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar85.4J/mol*KPHPMSCaldwell and Kebarle, 1984gas phase; M

N-Formylimidazole diethyl acetal + Water = Ethyl formate + 1H-Imidazole + Ethanol

By formula: C8H14N2O2 + H2O = C3H6O2 + C3H4N2 + C2H6O

Quantity Value Units Method Reference Comment
Deltar-34.6 ± 1.8kJ/molCmGuthrie and Pike, 1987liquid phase; Heat of hydrolysis; ALS

Ethyl orthoformate + Water = Ethyl formate + 2Ethanol

By formula: C7H16O3 + H2O = C3H6O2 + 2C2H6O

Quantity Value Units Method Reference Comment
Deltar-13.25 ± 0.79kJ/molCmHine and Klueppet, 1974liquid phase; Heat of hydrolysis; ALS

Ethane, 1,1,1-trimethoxy- + Water = Ethyl formate + 2Methyl Alcohol

By formula: C5H12O3 + H2O = C3H6O2 + 2CH4O

Quantity Value Units Method Reference Comment
Deltar-26.3 ± 2.7kJ/molCmHine and Klueppet, 1974liquid 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.

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]

Sieck and Meot-ner, 1989
Sieck, L.W.; Meot-ner, M., Ionic Hydrogen Bond and Ion Solvation. 8. RS-..HOR Bond Strengths. Correlation with Acidities., J. Phys. Chem., 1989, 93, 4, 1586, https://doi.org/10.1021/j100341a079 . [all data]

Caldwell and Kebarle, 1984
Caldwell, G.; Kebarle, P., Binding energies and structural effects in halide anion-ROH and -RCOOH complexes from gas phase equilibria measurements, J. Am. Chem. Soc., 1984, 106, 967. [all data]

Guthrie and Pike, 1987
Guthrie, J.P.; Pike, D.C., Hydration of acylimidazoles: tetrahedral intermediates in acylimidazole hydrolysis and nucleophilic attack by imidazole on esters. The question of concerted mechanisms for acyl transfers, Can. J. Chem., 1987, 65, 1951-1969. [all data]

Hine and Klueppet, 1974
Hine, J.; Klueppet, A.W., Structural effects on rates and equilibria. XVIII. Thermodynamic stability of ortho esters, J. Am. Chem. Soc., 1974, 96, 2924-2929. [all data]


Notes

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