Ketene

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Gas phase 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Δfgas-87.24kJ/molIonOrlov, Krivoruchko, et al., 1986Author was aware that data differs from previously reported values; ALS
Δfgas-48. ± 2.kJ/molCmNuttall, Laufer, et al., 1971ALS
Δfgas-61.84kJ/molCmRice and Greenberg, 1934ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
33.2650.Thermodynamics Research Center, 1997p=1 bar. Selected entropies and heat capacities are in excellent agreement with statistically calculated values [ Cox A.P., 1963, Moore C.B., 1963] and value of S(298.15 K) calculated by ab initio method [ East A.L.L., 1997]. Maximum discrepancies with earlier calculations [ Drayton L.G., 1948, Sundaram S., 1960] amount to 6 and 4 J/mol*K for S(T) and Cp(T), respectively. S(T) values calculated by [ Zhuravlev E.Z., 1959] are 11-13 J/mol*K lower than recommended ones.; GT
34.23100.
37.92150.
42.74200.
49.59273.15
51.75298.15
51.91300.
59.49400.
65.61500.
70.66600.
74.94700.
78.64800.
81.88900.
84.711000.
87.191100.
89.351200.
91.251300.
92.911400.
94.361500.

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry 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
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 • 4294967295Ketene) + Ketene = CAS Reg. No. 77213-00-4

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

Quantity Value Units Method Reference Comment
Δr181. ± 16.kJ/molN/AMarks, Brauman, et al., 1988gas phase; B
Δr187. ± 16.kJ/molTherFarid and McMahon, 1980gas phase; Between MeCOCH2F, cyclopentadiene; value altered from reference due to change in acidity scale; B
Δr186. ± 16.kJ/molN/AWenthold and Squires, 1995gas phase; Re-evaluation of literature thermo cycle; B
Δr148. ± 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
Δr115. ± 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 • Ketene)

By formula: F- + C2H2O = (F- • C2H2O)

Quantity Value Units Method Reference Comment
Δr148.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
Δr111.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
Δr115.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
Δr1526. ± 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
Δr1497. ± 8.4kJ/molIMRBOakes, Jones, et al., 1983gas phase; Acid: ketene; value altered from reference due to change in acidity scale; B

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

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

Quantity Value Units Method Reference Comment
Δr257. ± 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 • 4294967295Ketene) + Ketene = CAS Reg. No. 78944-68-0

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

Quantity Value Units Method Reference Comment
Δr143. ± 4.6kJ/molN/ANimlos, Soderquist, et al., 1989gas phase; B
Δr6.7 ± 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
Δr-208.2 ± 1.6kJ/molCmNuttall, Laufer, et al., 1971gas phase; ALS
Δr-197.3kJ/molCmRice and Greenberg, 1934gas phase; ALS

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

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

Quantity Value Units Method Reference Comment
Δr203. ± 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 • 4294967295Ketene) + Ketene = CAS Reg. No. 211040-82-3

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

Quantity Value Units Method Reference Comment
Δr122. ± 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
Δr94.7kJ/molEqkBlake and Speis, 1974gas phase; Heat of formation derived by 77PED/RYL; ALS

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

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

Quantity Value Units Method Reference Comment
Δr231. ± 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
Δr-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
Δr-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
Δr-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
Δr-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
Δr-98.28kJ/molCmRice and Greenberg, 1934liquid phase; ALS

Ketene + Isopropyl Alcohol = Isopropyl acetate

By formula: C2H2O + C3H8O = C5H10O2

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

Ketene + Thioacetic acid = Diacetyl sulphide

By formula: C2H2O + C2H4OS = C4H6O2S

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

Ketene + Ethanol = Ethyl Acetate

By formula: C2H2O + C2H6O = C4H8O2

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

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Orlov, Krivoruchko, et al., 1986
Orlov, V.M.; Krivoruchko, A.A.; Misharev, A.D.; Takhistov, V.V., Enthalpy of vapor phase formation of ketene, ethynol, and their analogs, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986, 2404-2405. [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]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Cox A.P., 1963
Cox A.P., Fundamental vibrational frequencies in ketene and the deuteroketenes, J. Chem. Phys., 1963, 38, 1636-1643. [all data]

Moore C.B., 1963
Moore C.B., Infrared spectrum and vibrational potential function of ketene and the deuterated ketenes, J. Chem. Phys., 1963, 38, 2816-2829. [all data]

East A.L.L., 1997
East A.L.L., Ab initio statistical thermodynamical models for the computation of third-law entropies, J. Chem. Phys., 1997, 106, 6655-6674. [all data]

Drayton L.G., 1948
Drayton L.G., The infrared spectrum of ketene, J. Chem. Soc., 1948, 1416-1419. [all data]

Sundaram S., 1960
Sundaram S., Potential energy constants, rotational distortion constants, and thermodynamic properties of H2C=C=O and D2C=C=O, J. Chem. Phys., 1960, 32, 1554-1556. [all data]

Zhuravlev E.Z., 1959
Zhuravlev E.Z., Isotopic effect on thermodynamic functions of some organic deuterocompounds in the ideal gas state, Tr. Khim. i Khim. Tekhnol., 1959, 2, 475-485. [all data]

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]

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, Gas phase thermochemistry data, Reaction thermochemistry data, References