CH2=CHO anion
- Formula: C2H3O-
- Molecular weight: 43.0452
- CAS Registry Number: 35731-40-9
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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, Ion clustering data, References, Notes
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
By formula: C2H3O- + H+ = C2H4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 366.42 ± 0.81 | kcal/mol | D-EA | Mead, Lykke, et al., 1984 | gas phase; Uncertainty: 6 millical/mol (0.26 micro-eV).Dipolebound state at ca. 14.3 cal/mol (5 cm-1); B |
ΔrH° | 365.8 ± 2.2 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas 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 |
ΔrH° | 366.5 ± 2.9 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 359.6 ± 1.2 | kcal/mol | H-TS | Mead, Lykke, et al., 1984 | gas phase; Uncertainty: 6 millical/mol (0.26 micro-eV).Dipolebound state at ca. 14.3 cal/mol (5 cm-1); B |
ΔrG° | 359.0 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas 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 |
ΔrG° | 359.7 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
By formula: C2H3O- + H2O = (C2H3O- • H2O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.4 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 19.5 | cal/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 9.6 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase; B |
(C2H3O- • 4294967295) + = C2H3O-
By formula: (C2H3O- • 4294967295C2H2O) + C2H2O = C2H3O-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 61.5 ± 2.3 | kcal/mol | N/A | Bartmess, Scott, et al., 1979 | gas 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
Go To: Top, Reaction thermochemistry data, Ion clustering data, References, Notes
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
By formula: C2H3O- + H+ = C2H4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 366.42 ± 0.81 | kcal/mol | D-EA | Mead, Lykke, et al., 1984 | gas phase; Uncertainty: 6 millical/mol (0.26 micro-eV).Dipolebound state at ca. 14.3 cal/mol (5 cm-1) |
ΔrH° | 365.8 ± 2.2 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas 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 |
ΔrH° | 366.5 ± 2.9 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 359.6 ± 1.2 | kcal/mol | H-TS | Mead, Lykke, et al., 1984 | gas phase; Uncertainty: 6 millical/mol (0.26 micro-eV).Dipolebound state at ca. 14.3 cal/mol (5 cm-1) |
ΔrG° | 359.0 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas 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 |
ΔrG° | 359.7 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase |
Ion clustering data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes
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- • 4294967295) + = C2H3O-
By formula: (C2H3O- • 4294967295C2H2O) + C2H2O = C2H3O-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 61.5 ± 2.3 | kcal/mol | N/A | Bartmess, Scott, et al., 1979 | gas 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 |
By formula: C2H3O- + H2O = (C2H3O- • H2O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.4 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 19.5 | cal/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 9.6 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas 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
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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