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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

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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

References

Go To: Top, Reaction thermochemistry 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]


Notes

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