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EtO anion


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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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Individual Reactions

C2H5O- + Ethanol = (C2H5O- bullet Ethanol)

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

Quantity Value Units Method Reference Comment
Deltar115. ± 4.2kJ/molTDEqMeot-Ner and Sieck, 1986gas phase; B,M
Deltar118. ± 10.kJ/molN/ACaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M
Quantity Value Units Method Reference Comment
Deltar112.J/mol*KPHPMSMeot-Ner and Sieck, 1986gas phase; M
Deltar123.J/mol*KN/ACaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH; Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Deltar82.0 ± 6.7kJ/molTDEqMeot-Ner and Sieck, 1986gas phase; B
Deltar79.5 ± 6.7kJ/molIMRECaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M
Deltar84.1kJ/molICRMcIver, Scott, et al., 1973gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; Meot-Ner (Mautner), 1992; M

C2H5O- + Methyl Alcohol = (C2H5O- bullet Methyl Alcohol)

By formula: C2H5O- + CH4O = (C2H5O- bullet CH4O)

Quantity Value Units Method Reference Comment
Deltar114. ± 12.kJ/molIMRECaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M
Deltar107. ± 7.9kJ/molCIDTDeTuri and Ervin, 1999gas phase; B
Quantity Value Units Method Reference Comment
Deltar123.J/mol*KN/ACaldwell, Rozeboom, et al., 1984gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M
Quantity Value Units Method Reference Comment
Deltar77.8 ± 8.4kJ/molIMRECaldwell, Rozeboom, et al., 1984gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
56.1296.FAMackay, Rakshit, et al., 1982gas phase; From thermochemical cycle,switching reaction(CH3O-)CH3OH; Caldwell and Kebarle, 1986, Taft, 1983; M

C2H5O- + Hydrogen cation = Ethanol

By formula: C2H5O- + H+ = C2H6O

Quantity Value Units Method Reference Comment
Deltar1587. ± 4.2kJ/molD-EARamond, Davico, et al., 2000gas phase; B
Deltar1582. ± 8.4kJ/molCIDCHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Deltar1579. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar1586.2 ± 0.42kJ/molCIDTDeTuri and Ervin, 1999gas phase; B
Quantity Value Units Method Reference Comment
Deltar1559. ± 4.6kJ/molH-TSRamond, Davico, et al., 2000gas phase; B
Deltar1554. ± 8.8kJ/molH-TSHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Deltar1551. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

(C2H5O- bullet 4294967295Acetaldehyde) + Acetaldehyde = C2H5O-

By formula: (C2H5O- bullet 4294967295C2H4O) + C2H4O = C2H5O-

Quantity Value Units Method Reference Comment
Deltar158. ± 4.2kJ/molN/ARamond, Davico, et al., 2000gas phase; B
Deltar165. ± 9.2kJ/molTherBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

C2H5O- + Fluoroform = C3H6F3O-

By formula: C2H5O- + CHF3 = C3H6F3O-

Quantity Value Units Method Reference Comment
Deltar92.0 ± 4.2kJ/molIMREChabinyc and Brauman, 1998gas phase; B
Quantity Value Units Method Reference Comment
Deltar63.2 ± 4.2kJ/molIMREChabinyc and Brauman, 1998gas phase; B

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 and Sieck, 1986
Meot-Ner, M.; Sieck, L.W., The ionic hydrogen bond and ion solvation. 5. OH...O- bonds. Gas phase solvation and clustering of alkoxide and carboxylate anions, J. Am. Chem. Soc., 1986, 108, 7525. [all data]

Caldwell, Rozeboom, et al., 1984
Caldwell, G.; Rozeboom, M.D.; Kiplinger, J.P.; Bartmess, J.E., Anion-alcohol hydrogen bond strengths in the gas phase, J. Am. Chem. Soc., 1984, 106, 4660. [all data]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Thermodynamics of the Association Reactions OH- - H2O = HOHOH- and CH3O- - CH3OH = CH3OHOCH3- in the Gas Phase, J. Phys. Chem., 1990, 94, 12, 5184, https://doi.org/10.1021/j100375a076 . [all data]

Meot-ner and Sieck, 1986
Meot-ner, M.; Sieck, L.W., Relative acidities of water and methanol, and the stabilities of the dimer adducts, J. Phys. Chem., 1986, 90, 6687. [all data]

Meot-Ner(Mautner), 1986
Meot-Ner(Mautner), M., Comparative Stabilities of Cationic and Anionic Hydrogen-Bonded Networks. Mixed Clusters of Water-Methanol, J. Am. Chem. Soc., 1986, 108, 20, 6189, https://doi.org/10.1021/ja00280a014 . [all data]

McIver, Scott, et al., 1973
McIver, R.T., Jr.; Scott, J.A.; Riveros, J.M., Effect of solvation on the intrinsic relative acidity of methanol and ethanol, J. Am. Chem. Soc., 1973, 95, 2706. [all data]

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]

DeTuri and Ervin, 1999
DeTuri, V.F.; Ervin, K.M., Competitive threshold collision-induced dissociation: Gas-phase acidities and bond dissociation energies for a series of alcohols, J. Phys. Chem. A, 1999, 103, 35, 6911-6920, https://doi.org/10.1021/jp991459m . [all data]

Mackay, Rakshit, et al., 1982
Mackay, G.I.; Rakshit, A.B.; Bohme, D.K., An Experimental Study of the Reactivity and Relative Basicity of the Methoxide Anion in the Gas Phase at Room Temperature, and their Perturbation by Methanol Solvent, Can. J. Chem., 1982, 60, 20, 2594, https://doi.org/10.1139/v82-373 . [all data]

Caldwell and Kebarle, 1986
Caldwell, G.; Kebarle, P., Mobility of Gaseous Ions in Weak Electric Fields in Unpublished results, 1986. [all data]

Taft, 1983
Taft, R.W., Protonic acidities and basicities in the gas phase and in solution: Substiuent and solvent effects, Prog. Phys. Org. Chem., 1983, 14, 247. [all data]

Ramond, Davico, et al., 2000
Ramond, T.M.; Davico, G.E.; Schwartz, R.L.; Lineberger, W.C., Vibronic structure of alkoxy radicals via photoelectron spectroscopy, J. Chem. Phys., 2000, 112, 3, 1158-1169, https://doi.org/10.1063/1.480767 . [all data]

Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G., The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols, Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W . [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]

Chabinyc and Brauman, 1998
Chabinyc, M.L.; Brauman, J.I., Acidity, basicity, and the stability of hydrogen bonds: Complexes of RO-+HCF3, J. Am. Chem. Soc., 1998, 120, 42, 10863-10870, https://doi.org/10.1021/ja9817592 . [all data]


Notes

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