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CH2=CHO 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

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

C2H3O- + Hydrogen cation = Acetaldehyde

By formula: C2H3O- + H+ = C2H4O

Quantity Value Units Method Reference Comment
Deltar366.42 ± 0.81kcal/molD-EAMead, Lykke, et al., 1984gas phase; Uncertainty: 6 millical/mol (0.26 micro-eV).Dipolebound state at ca. 14.3 cal/mol (5 cm-1); B
Deltar365.8 ± 2.2kcal/molG+TSBartmess, Scott, et al., 1979gas phase; Acid: ethanal. The enol is 9.6 kcal/mol more acidic: Holmes and Lossing, 1982; value altered from reference due to change in acidity scale; B
Deltar366.5 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Deltar359.6 ± 1.2kcal/molH-TSMead, Lykke, et al., 1984gas phase; Uncertainty: 6 millical/mol (0.26 micro-eV).Dipolebound state at ca. 14.3 cal/mol (5 cm-1); B
Deltar359.0 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; Acid: ethanal. The enol is 9.6 kcal/mol more acidic: Holmes and Lossing, 1982; value altered from reference due to change in acidity scale; B
Deltar359.7 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

C2H3O- + Water = (C2H3O- bullet Water)

By formula: C2H3O- + H2O = (C2H3O- bullet H2O)

Quantity Value Units Method Reference Comment
Deltar15.4 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar19.5cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar9.6 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B

(C2H3O- bullet 4294967295Ketene) + Ketene = C2H3O-

By formula: (C2H3O- bullet 4294967295C2H2O) + C2H2O = C2H3O-

Quantity Value Units Method Reference Comment
Deltar61.5 ± 2.3kcal/molN/ABartmess, Scott, et al., 1979gas phase; Acid: ethanal. The enol is 9.6 kcal/mol more acidic: Holmes and Lossing, 1982; value altered from reference due to change in acidity scale; B

Gas phase ion energetics 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: John E. Bartmess

Protonation reactions

C2H3O- + Hydrogen cation = Acetaldehyde

By formula: C2H3O- + H+ = C2H4O

Quantity Value Units Method Reference Comment
Deltar366.42 ± 0.81kcal/molD-EAMead, Lykke, et al., 1984gas phase; Uncertainty: 6 millical/mol (0.26 micro-eV).Dipolebound state at ca. 14.3 cal/mol (5 cm-1)
Deltar365.8 ± 2.2kcal/molG+TSBartmess, Scott, et al., 1979gas phase; Acid: ethanal. The enol is 9.6 kcal/mol more acidic: Holmes and Lossing, 1982; value altered from reference due to change in acidity scale
Deltar366.5 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar359.6 ± 1.2kcal/molH-TSMead, Lykke, et al., 1984gas phase; Uncertainty: 6 millical/mol (0.26 micro-eV).Dipolebound state at ca. 14.3 cal/mol (5 cm-1)
Deltar359.0 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; Acid: ethanal. The enol is 9.6 kcal/mol more acidic: Holmes and Lossing, 1982; value altered from reference due to change in acidity scale
Deltar359.7 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase

Ion clustering 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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

(C2H3O- bullet 4294967295Ketene) + Ketene = C2H3O-

By formula: (C2H3O- bullet 4294967295C2H2O) + C2H2O = C2H3O-

Quantity Value Units Method Reference Comment
Deltar61.5 ± 2.3kcal/molN/ABartmess, Scott, et al., 1979gas phase; Acid: ethanal. The enol is 9.6 kcal/mol more acidic: Holmes and Lossing, 1982; value altered from reference due to change in acidity scale; B

C2H3O- + Water = (C2H3O- bullet Water)

By formula: C2H3O- + H2O = (C2H3O- bullet H2O)

Quantity Value Units Method Reference Comment
Deltar15.4 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar19.5cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar9.6 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Notes

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

Mead, Lykke, et al., 1984
Mead, R.D.; Lykke, K.R.; Lineberger, W.C.; Marks, J.; Brauman, J.I., Spectroscopy and Dynamics of the Dipole-Bound State of Acetaldehyde Enolate., J. Chem. Phys., 1984, 81, 11, 4883., https://doi.org/10.1063/1.447515 . [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]

Holmes and Lossing, 1982
Holmes, J.L.; Lossing, F.P., Heats of formation of the ionic and neutral enols of acetaldehyde and acetone, J. Am. Chem. Soc., 1982, 104, 2648. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Meot-ner, 1988
Meot-ner, M., The Ionic Hydrogen Bond and Solvation. 7. Interaction Energies of Carbanions with Solvent Molecules, J. Am. Chem. Soc., 1988, 110, 12, 3858, https://doi.org/10.1021/ja00220a022 . [all data]


Notes

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