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
Δr366.42 ± 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
Δr365.8 ± 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
Δr366.5 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Δr359.6 ± 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
Δr359.0 ± 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
Δr359.7 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B

C2H3O- + Water = (C2H3O- • Water)

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

Quantity Value Units Method Reference Comment
Δr15.4 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr19.5cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr9.6 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B

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

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

Quantity Value Units Method Reference Comment
Δr61.5 ± 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
Δr366.42 ± 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)
Δr365.8 ± 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
Δr366.5 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr359.6 ± 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)
Δr359.0 ± 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
Δr359.7 ± 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- • 4294967295Ketene) + Ketene = C2H3O-

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

Quantity Value Units Method Reference Comment
Δr61.5 ± 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- • Water)

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

Quantity Value Units Method Reference Comment
Δr15.4 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Δr19.5cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Δr9.6 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B

References

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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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