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Ketene

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Reaction thermochemistry data

Go To: Top, 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

(CAS Reg. No. 77213-00-4 bullet 4294967295Ketene) + Ketene = CAS Reg. No. 77213-00-4

By formula: (CAS Reg. No. 77213-00-4 bullet 4294967295C2H2O) + C2H2O = CAS Reg. No. 77213-00-4

Quantity Value Units Method Reference Comment
Deltar181. ± 16.kJ/molN/AMarks, Brauman, et al., 1988gas phase; B
Deltar187. ± 16.kJ/molTherFarid and McMahon, 1980gas phase; Between MeCOCH2F, cyclopentadiene; value altered from reference due to change in acidity scale; B
Deltar186. ± 16.kJ/molN/AWenthold and Squires, 1995gas phase; Re-evaluation of literature thermo cycle; B
Deltar148. ± 8.4kJ/molIMRELarson and McMahon, 1983gas phase; These relative affinities are ca. 10 kcal/mol weaker than threshold values (see Wenthold and Squires, 1995) for donors greater than ca. 27 kcal/mol in free energy. This discrepancy has not yet been resolved, though the stronger value appears preferable.; B
Quantity Value Units Method Reference Comment
Deltar115. ± 8.4kJ/molIMRELarson and McMahon, 1983gas phase; These relative affinities are ca. 10 kcal/mol weaker than threshold values (see Wenthold and Squires, 1995) for donors greater than ca. 27 kcal/mol in free energy. This discrepancy has not yet been resolved, though the stronger value appears preferable.; B

Fluorine anion + Ketene = (Fluorine anion bullet Ketene)

By formula: F- + C2H2O = (F- bullet C2H2O)

Quantity Value Units Method Reference Comment
Deltar148.kJ/molICRLarson and McMahon, 1983gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity Value Units Method Reference Comment
Deltar111.J/mol*KN/ALarson and McMahon, 1983gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity Value Units Method Reference Comment
Deltar115.kJ/molICRLarson and McMahon, 1983gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M

C2HO- + Hydrogen cation = Ketene

By formula: C2HO- + H+ = C2H2O

Quantity Value Units Method Reference Comment
Deltar1526. ± 8.8kJ/molG+TSOakes, Jones, et al., 1983gas phase; Acid: ketene; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1497. ± 8.4kJ/molIMRBOakes, Jones, et al., 1983gas phase; Acid: ketene; value altered from reference due to change in acidity scale; B

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

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

Quantity Value Units Method Reference Comment
Deltar257. ± 9.6kJ/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

(CAS Reg. No. 78944-68-0 bullet 4294967295Ketene) + Ketene = CAS Reg. No. 78944-68-0

By formula: (CAS Reg. No. 78944-68-0 bullet 4294967295C2H2O) + C2H2O = CAS Reg. No. 78944-68-0

Quantity Value Units Method Reference Comment
Deltar143. ± 4.6kJ/molN/ANimlos, Soderquist, et al., 1989gas phase; B
Deltar6.7 ± 9.2kJ/molTherDePuy, Bierbaum, et al., 1985gas phase; B

Sodium hydroxide + Ketene = Acetic acid, sodium salt

By formula: HNaO + C2H2O = C2H3NaO2

Quantity Value Units Method Reference Comment
Deltar-208.2 ± 1.6kJ/molCmNuttall, Laufer, et al., 1971gas phase; ALS
Deltar-197.3kJ/molCmRice and Greenberg, 1934gas phase; ALS

(CAS Reg. No. 64723-96-2 bullet 4294967295Ketene) + Ketene = CAS Reg. No. 64723-96-2

By formula: (CAS Reg. No. 64723-96-2 bullet 4294967295C2H2O) + C2H2O = CAS Reg. No. 64723-96-2

Quantity Value Units Method Reference Comment
Deltar203. ± 9.6kJ/molN/ABartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

(CAS Reg. No. 211040-82-3 bullet 4294967295Ketene) + Ketene = CAS Reg. No. 211040-82-3

By formula: (CAS Reg. No. 211040-82-3 bullet 4294967295C2H2O) + C2H2O = CAS Reg. No. 211040-82-3

Quantity Value Units Method Reference Comment
Deltar122. ± 12.kJ/molN/ATaft, 1987gas phase; value altered from reference due to change in acidity scale; B

Diacetyl sulphide = Ketene + Thioacetic acid

By formula: C4H6O2S = C2H2O + C2H4OS

Quantity Value Units Method Reference Comment
Deltar94.7kJ/molEqkBlake and Speis, 1974gas phase; Heat of formation derived by 77PED/RYL; ALS

(CAS Reg. No. 84148-57-2 bullet 4294967295Ketene) + Ketene = CAS Reg. No. 84148-57-2

By formula: (CAS Reg. No. 84148-57-2 bullet 4294967295C2H2O) + C2H2O = CAS Reg. No. 84148-57-2

Quantity Value Units Method Reference Comment
Deltar231. ± 13.kJ/molN/AGrabowski and Cheng, 1989gas phase; B

Ketene + Acetic acid = Acetic anhydride

By formula: C2H2O + C2H4O2 = C4H6O3

Quantity Value Units Method Reference Comment
Deltar-87.5 ± 2.2kJ/molEqkBlake, Davies, et al., 1971gas phase; ALS

Ketene + 1-Butanol = Acetic acid, butyl ester

By formula: C2H2O + C4H10O = C6H12O2

Quantity Value Units Method Reference Comment
Deltar-146.9kJ/molCmRice and Greenberg, 1934liquid phase; ALS

Ketene + 1-Propanol, 2-methyl- = Isobutyl acetate

By formula: C2H2O + C4H10O = C6H12O2

Quantity Value Units Method Reference Comment
Deltar-143.8kJ/molCmRice and Greenberg, 1934liquid phase; ALS

Ketene + 2-Butanol = sec-Butyl acetate

By formula: C2H2O + C4H10O = C6H12O2

Quantity Value Units Method Reference Comment
Deltar-144.5kJ/molCmRice and Greenberg, 1934liquid phase; ALS

Ketene + 2-Propanol, 2-methyl- = Acetic acid, 1,1-dimethylethyl ester

By formula: C2H2O + C4H10O = C6H12O2

Quantity Value Units Method Reference Comment
Deltar-98.28kJ/molCmRice and Greenberg, 1934liquid phase; ALS

Ketene + Isopropyl Alcohol = Isopropyl acetate

By formula: C2H2O + C3H8O = C5H10O2

Quantity Value Units Method Reference Comment
Deltar-150.2kJ/molCmRice and Greenberg, 1934liquid phase; ALS

Ketene + Thioacetic acid = Diacetyl sulphide

By formula: C2H2O + C2H4OS = C4H6O2S

Quantity Value Units Method Reference Comment
Deltar-94.7kJ/molEqkBlake and Speis, 1974gas phase; ALS

Ketene + Ethanol = Ethyl Acetate

By formula: C2H2O + C2H6O = C4H8O2

Quantity Value Units Method Reference Comment
Deltar-152.5kJ/molCmRice and Greenberg, 1934gas phase; ALS

Ketene + 1-Propanol = n-Propyl acetate

By formula: C2H2O + C3H8O = C5H10O2

Quantity Value Units Method Reference Comment
Deltar-147.8kJ/molCmRice and Greenberg, 1934gas phase; ALS

Ketene + Methyl Alcohol = Acetic acid, methyl ester

By formula: C2H2O + CH4O = C3H6O2

Quantity Value Units Method Reference Comment
Deltar-154.5kJ/molCmRice and Greenberg, 1934gas phase; ALS

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.

Marks, Brauman, et al., 1988
Marks, J.; Brauman, J.I.; Mead, R.D.; Lykke, K.R.; Lineberger, W.C., Spectroscopy and Dynamics of the Dipole Supported State of Acetyl Fluoride Enolate Anion, J. Chem. Phys., 1988, 88, 11, 6785, https://doi.org/10.1063/1.454424 . [all data]

Farid and McMahon, 1980
Farid, R.; McMahon, T.B., The gas phase acidities of fluorinated acetones. An ICR investigation of the role of fluorine substituents in the stabilization of planar carbanions, Can. J. Chem., 1980, 58, 2307. [all data]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Bond dissociation energies of F2(-) and HF2(-). A gas-phase experimental and G2 theoretical study, J. Phys. Chem., 1995, 99, 7, 2002, https://doi.org/10.1021/j100007a034 . [all data]

Larson and McMahon, 1983
Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

Arshadi, Yamdagni, et al., 1970
Arshadi, M.; Yamdagni, R.; Kebarle, P., Hydration of Halide Negative Ions in the Gas Phase. II. Comparison of Hydration Energies for the Alkali Positive and Halide Negative Ions, J. Phys. Chem., 1970, 74, 7, 1475, https://doi.org/10.1021/j100702a014 . [all data]

Oakes, Jones, et al., 1983
Oakes, J.M.; Jones, M.E.; Bierbaum, V.M.; Ellison, G.B., Photoelectron spectroscopy of CCO- and HCCO-, J. Phys. Chem., 1983, 87, 4810. [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]

Nimlos, Soderquist, et al., 1989
Nimlos, M.R.; Soderquist, J.A.; Ellison, G.B., Spectroscopy of CH3CO- and CH3CO, J. Am. Chem. Soc., 1989, 111, 20, 7675, https://doi.org/10.1021/ja00202a001 . [all data]

DePuy, Bierbaum, et al., 1985
DePuy, C.H.; Bierbaum, V.M.; Damrauer, R.; Soderquist, J.A., Gas-phase reactions of the acetyl anion, J. Am. Chem. Soc., 1985, 107, 3385. [all data]

Nuttall, Laufer, et al., 1971
Nuttall, R.L.; Laufer, A.H.; Kilday, M.V., The enthalpy of formation of ketene, J. Chem. Thermodyn., 1971, 3, 167-174. [all data]

Rice and Greenberg, 1934
Rice, F.O.; Greenberg, J., Ketene. III. Heat of formation and heat of reaction with alcohols, J. Am. Chem. Soc., 1934, 38, 2268-2270. [all data]

Taft, 1987
Taft, R.W., The Nature and Analysis of Substitutent Electronic Effects, Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Blake and Speis, 1974
Blake, P.G.; Speis, A., Reactions of keten. Part IV. Kinetics and thermodynamics of the gas-phase reaction: Thioacetic acid + keten = acetic Thioanhydride, J. Chem. Soc. Perkin Trans. 2, 1974, 1879-1881. [all data]

Grabowski and Cheng, 1989
Grabowski, J.J.; Cheng, X., Gas-Phase Formation of the Enolate Monoanion of Acetic Acid by Proton Abstraction, J. Am. Chem. Soc., 1989, 111, 8, 3106, https://doi.org/10.1021/ja00190a078 . [all data]

Blake, Davies, et al., 1971
Blake, P.G.; Davies, H.H.; Speis, A., Reactions of keten. Part II. The thermodynamics of the gas-phase equilibrium: acetic acid + keten = acetic anhydride, J. Chem. Soc. B, 1971, 2050-2052. [all data]


Notes

Go To: Top, Reaction thermochemistry data, References