CH2=C(Me)O anion
- Formula: C3H5O-
- Molecular weight: 57.0717
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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
Electron affinity of neutral species
EAneutral (eV) | Method | Reference | Comment |
---|---|---|---|
1.7470 ± 0.0020 | N/A | Yacovitch, Garand, et al., 2010 | Vertical Detachment Energy: 1.759±0.002 eV |
1.758 ± 0.019 | LPD | Brinkman, Berger, et al., 1993 | |
1.757 ± 0.033 | LPES | Ellison, Engleking, et al., 1982 | |
1.75 ± 0.13 | D-EA | Bartmess, Scott, et al., 1979 | value altered from reference due to change in acidity scale |
1.760 ± 0.020 | LPES | Alconcel, Deyerl, et al., 2001 | |
1.761 ± 0.056 | PD | Zimmerman, Reed, et al., 1977 |
Protonation reactions
By formula: C3H5O- + H+ = C3H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 368.8 ± 2.1 | kcal/mol | D-EA | Brinkman, Berger, et al., 1993 | gas phase |
ΔrH° | 369.0 ± 2.1 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale |
ΔrH° | 369.6 ± 2.6 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase |
ΔrH° | 367.6 ± 1.8 | kcal/mol | EIAE | Muftakhov, Vasil'ev, et al., 1999 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 361.9 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale |
ΔrG° | 362.4 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas 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 by: John E. Bartmess
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
By formula: C3H5O- + C2H3N = (C3H5O- • C2H3N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.3 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 9.6 ± 2.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase |
By formula: C3H5O- + C3H6O = (C3H5O- • C3H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | >25.90 | kcal/mol | IMRB | Sheldon and Bowie, 1983 | gas phase; MeOH..F- + Me2CO -> |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | >19.70 | kcal/mol | IMRB | Sheldon and Bowie, 1983 | gas phase; MeOH..F- + Me2CO -> |
By formula: C3H5O- + C3H8O = (C3H5O- • C3H8O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 21.6 ± 2.9 | kcal/mol | N/A | Caldwell, Rozeboom, et al., 1984 | gas 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 |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 12.9 ± 2.0 | kcal/mol | IMRE | Caldwell, Rozeboom, et al., 1984 | gas 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 |
By formula: C3H5O- + H2O = (C3H5O- • H2O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.8 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 9.7 ± 1.0 | kcal/mol | TDAs | Meot-ner, 1988 | gas phase |
References
Go To: Top, 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.
Yacovitch, Garand, et al., 2010
Yacovitch, T.I.; Garand, E.; Neumark, D.M.,
Slow Photoelectron Velocity-Map Imaging of the i-Methylvinoxide Anion,
J. Phys. Chem. A, 2010, 114, 42, 11091-11099, https://doi.org/10.1021/jp101930b
. [all data]
Brinkman, Berger, et al., 1993
Brinkman, E.A.; Berger, S.; Marks, J.; Brauman, J.I.,
Molecular Rotation and the Observation of Dipole-Bound States of Anions,
J. Chem. Phys., 1993, 99, 10, 7586, https://doi.org/10.1063/1.465688
. [all data]
Ellison, Engleking, et al., 1982
Ellison, G.B.; Engleking, P.C.; Lineberger, W.C.,
Photoelectron spectroscopy of alkoxide and enolate negative ions,
J. Phys. Chem., 1982, 86, 4873. [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]
Alconcel, Deyerl, et al., 2001
Alconcel, L.S.; Deyerl, H.J.; Continetti, R.E.,
Effects of alkyl substitution on the energetics of enolate anions and radicals,
J. Am. Chem. Soc., 2001, 123, 50, 12675-12681, https://doi.org/10.1021/ja0120431
. [all data]
Zimmerman, Reed, et al., 1977
Zimmerman, A.H.; Reed, K.J.; Brauman, J.I.,
Photodetachment of electrons from enolate anions. Gas phase electron affinities of enolate radicals,
J. Am. Chem. Soc., 1977, 99, 7203. [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]
Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Mazunov, V.A.,
Determination of electron affinity of carbonyl radicals by means of negative ion mass spectrometry,
Rapid Commun. Mass Spectrom., 1999, 13, 12, 1104-1108, https://doi.org/10.1002/(SICI)1097-0231(19990630)13:12<1104::AID-RCM619>3.0.CO;2-C
. [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]
Sheldon and Bowie, 1983
Sheldon, J.C.; Bowie, J.H.,
The Reactions of {F-..HOMe} and {MeCO2-..HF} Negative Ions with Acetaldehyde and Acetone.,
Aust. J. Chem., 1983, 36, 2, 289, https://doi.org/10.1071/CH9830289
. [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]
Notes
Go To: Top, Gas phase ion energetics data, Ion clustering data, References
- Symbols used in this document:
EAneutral Electron affinity of neutral species ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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