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CH2=C(Me)O 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 by: John E. Bartmess

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

C3H5O- + Hydrogen cation = Acetone

By formula: C3H5O- + H+ = C3H6O

Quantity Value Units Method Reference Comment
Deltar1543. ± 8.8kJ/molD-EABrinkman, Berger, et al., 1993gas phase
Deltar1544. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1546. ± 11.kJ/molG+TSCumming and Kebarle, 1978gas phase
Deltar1538. ± 7.5kJ/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase
Quantity Value Units Method Reference Comment
Deltar1514. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1516. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C3H5O- + 1-Propanol = (C3H5O- bullet 1-Propanol)

By formula: C3H5O- + C3H8O = (C3H5O- bullet C3H8O)

Quantity Value Units Method Reference Comment
Deltar90. ± 12.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
Quantity Value Units Method Reference Comment
Deltar54.0 ± 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

C3H5O- + Acetone = (C3H5O- bullet Acetone)

By formula: C3H5O- + C3H6O = (C3H5O- bullet C3H6O)

Quantity Value Units Method Reference Comment
Deltar>108.4kJ/molIMRBSheldon and Bowie, 1983gas phase; MeOH..F- + Me2CO ->
Quantity Value Units Method Reference Comment
Deltar>82.42kJ/molIMRBSheldon and Bowie, 1983gas phase; MeOH..F- + Me2CO ->

C3H5O- + Water = (C3H5O- bullet Water)

By formula: C3H5O- + H2O = (C3H5O- bullet H2O)

Quantity Value Units Method Reference Comment
Deltar66.1 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase
Quantity Value Units Method Reference Comment
Deltar41. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase

C3H5O- + Acetonitrile = (C3H5O- bullet Acetonitrile)

By formula: C3H5O- + C2H3N = (C3H5O- bullet C2H3N)

Quantity Value Units Method Reference Comment
Deltar64.0 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase
Quantity Value Units Method Reference Comment
Deltar40. ± 8.4kJ/molTDAsMeot-ner, 1988gas phase

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

Electron affinity of neutral species

EAneutral (eV) Method Reference Comment
1.7470 ± 0.0020N/AYacovitch, Garand, et al., 2010Vertical Detachment Energy: 1.759±0.002 eV
1.758 ± 0.019LPDBrinkman, Berger, et al., 1993 
1.757 ± 0.033LPESEllison, Engleking, et al., 1982 
1.75 ± 0.13D-EABartmess, Scott, et al., 1979value altered from reference due to change in acidity scale
1.760 ± 0.020LPESAlconcel, Deyerl, et al., 2001 
1.761 ± 0.056PDZimmerman, Reed, et al., 1977 

Protonation reactions

C3H5O- + Hydrogen cation = Acetone

By formula: C3H5O- + H+ = C3H6O

Quantity Value Units Method Reference Comment
Deltar1543. ± 8.8kJ/molD-EABrinkman, Berger, et al., 1993gas phase
Deltar1544. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1546. ± 11.kJ/molG+TSCumming and Kebarle, 1978gas phase
Deltar1538. ± 7.5kJ/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase
Quantity Value Units Method Reference Comment
Deltar1514. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1516. ± 8.4kJ/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 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

C3H5O- + Acetonitrile = (C3H5O- bullet Acetonitrile)

By formula: C3H5O- + C2H3N = (C3H5O- bullet C2H3N)

Quantity Value Units Method Reference Comment
Deltar64.0 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase
Quantity Value Units Method Reference Comment
Deltar40. ± 8.4kJ/molTDAsMeot-ner, 1988gas phase

C3H5O- + Acetone = (C3H5O- bullet Acetone)

By formula: C3H5O- + C3H6O = (C3H5O- bullet C3H6O)

Quantity Value Units Method Reference Comment
Deltar>108.4kJ/molIMRBSheldon and Bowie, 1983gas phase; MeOH..F- + Me2CO ->
Quantity Value Units Method Reference Comment
Deltar>82.42kJ/molIMRBSheldon and Bowie, 1983gas phase; MeOH..F- + Me2CO ->

C3H5O- + 1-Propanol = (C3H5O- bullet 1-Propanol)

By formula: C3H5O- + C3H8O = (C3H5O- bullet C3H8O)

Quantity Value Units Method Reference Comment
Deltar90. ± 12.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
Quantity Value Units Method Reference Comment
Deltar54.0 ± 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

C3H5O- + Water = (C3H5O- bullet Water)

By formula: C3H5O- + H2O = (C3H5O- bullet H2O)

Quantity Value Units Method Reference Comment
Deltar66.1 ± 4.2kJ/molTDAsMeot-ner, 1988gas phase
Quantity Value Units Method Reference Comment
Deltar41. ± 4.2kJ/molTDAsMeot-ner, 1988gas phase

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.

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]

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]

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]

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]

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]

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]

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]

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]

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]


Notes

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