Ketene

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Reaction thermochemistry data

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

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

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C2H2O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.617 ± 0.003eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)825.3kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity793.6kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Δf(+) ion879.kJ/molN/AN/A 
Quantity Value Units Method Reference Comment
ΔfH(+) ion,0K883.kJ/molN/AN/A 

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
822.9 ± 3.4Bouchoux and Salpin, 1999T = 302K; Re-evaluated thermokinetic parametric fitting by the authors using reference base GBs and PAs from Hunter and Lias, 1998; MM
822.9 ± 3.4Bouchoux and Salpin, 1999T = 298K; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
790.1 ± 1.5Bouchoux and Salpin, 1999T = 302K; Re-evaluated thermokinetic parametric fitting by the authors using reference base GBs and PAs from Hunter and Lias, 1998; MM
790.1 ± 1.5Bouchoux and Salpin, 1999T = 298K; MM

Ionization energy determinations

IE (eV) Method Reference Comment
9.6191 ± 0.0004PENiu, Bai, et al., 1993LL
9.614 ± 0.008PIVogt, Williamson, et al., 1978LLK
9.61 ± 0.02PEVogt, Williamson, et al., 1978LLK
9.63 ± 0.02PEHall, Maier, et al., 1977LLK
9.64PEBaker and Turner, 1969RDSH
9.61 ± 0.02SPrice, Teegan, et al., 1951RDSH
9.64PEBock, Hirabayashi, et al., 1981Vertical value; LLK
9.60PEBock, Hirabayashi, et al., 1977Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CHO+16.1 ± 0.4CHEICollin and Locht, 1970RDSH
CH2+13.729 ± 0.008CODERMcCulloh and Dibeler, 1976T = 0K; LLK
CH2+13.712 ± 0.008COPIMcCulloh and Dibeler, 1976T = 400K; LLK
CH2+13.8 ± 0.2COEICollin and Locht, 1970RDSH
CO+13.6 ± 0.3?EICollin and Locht, 1970RDSH
C2HO+14.9 ± 0.3HEICollin and Locht, 1970RDSH

De-protonation reactions

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

Mass spectrum (electron ionization)

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

Due to licensing restrictions, this spectrum cannot be downloaded.

Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
NIST MS number 55

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Bouchoux and Salpin, 1999
Bouchoux, J.; Salpin, J.Y., Re-evaluated gas-phase basicity and proton affinity data from the thermokinetic method, Rapid Com. Mass Spectrom., 1999, 13, 932. [all data]

Niu, Bai, et al., 1993
Niu, B.; Bai, Y.; Shirley, D.A., High resolution photoelectron spectroscopy and femtosecond intramolecular dynamics of H2CCO+ and D2CCO+, J. Chem. Phys., 1993, 99, 2520. [all data]

Vogt, Williamson, et al., 1978
Vogt, J.; Williamson, A.D.; Beauchamp, J.L., Properties and reactions of ketene in the gas phase by ion cyclotron resonance spectroscopy and photoionization mass spectrometry. Proton affinity, site specificity of protonation, and heat of formation of ketene, J. Am. Chem. Soc., 1978, 100, 3478. [all data]

Hall, Maier, et al., 1977
Hall, D.; Maier, J.P.; Rosmus, P., Electronic states of ketene radical cation, Chem. Phys., 1977, 24, 373. [all data]

Baker and Turner, 1969
Baker, C.; Turner, D.W., Photoelectron spectra of allene and keten; Jahn-Teller distortion in the ionisation of allene, Chem. Commun., 1969, 480. [all data]

Price, Teegan, et al., 1951
Price, W.C.; Teegan, J.P.; Walsh, A.D., The absorption spectrum of ketene in the far ultra-violet, J. Chem. Soc., 1951, 920. [all data]

Bock, Hirabayashi, et al., 1981
Bock, H.; Hirabayashi, T.; Mohmand, S., Thermische erzeugung von alkyl- und halogenketenen, Chem. Ber., 1981, 114, 2595. [all data]

Bock, Hirabayashi, et al., 1977
Bock, H.; Hirabayashi, T.; Mohmand, S.; Solouki, B., Instabile Zwischenprodukte in der Gasphase: Der thermische Zerfall von Carbonsaurechloriden RCOCl, Angew. Chem., 1977, 89, 106. [all data]

Collin and Locht, 1970
Collin, J.E.; Locht, R., Positive and negative ion formation in ketene by electron impact, Intern. J. Mass Spectrom. Ion Phys., 1970, 3, 465. [all data]

McCulloh and Dibeler, 1976
McCulloh, K.E.; Dibeler, V.H., Enthalpy of formation of methyl and methylene radicals of photoionization studies of methane and ketene, J. Chem. Phys., 1976, 64, 4445. [all data]


Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References