Ketene
- Formula: C2H2O
- Molecular weight: 42.0367
- IUPAC Standard InChIKey: CCGKOQOJPYTBIH-UHFFFAOYSA-N
- CAS Registry Number: 463-51-4
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Ethenone; Carbomethene; CH2CO; Keto-ethylene
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Phase change data
Go To: Top, Gas phase ion energetics 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔvapH° | 4.9 ± 1.4 | kcal/mol | V | Reuben, 1969 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
4.88 ± 0.02 | 209. | A,MM | Stephenson and Malanowski, 1987 | Based on data from 159. to 224. K. See also Reuben, 1969, 2.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
159.3 to 223.80 | 3.97151 | 766.685 | -30.609 | Reuben, 1969, 2 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics data
Go To: Top, Phase change 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 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 ± 0.003 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 197.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 189.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°(+) ion | 210. | kcal/mol | N/A | N/A | |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH(+) ion,0K | 211. | kcal/mol | N/A | N/A |
Proton affinity at 298K
Proton affinity (kcal/mol) | Reference | Comment |
---|---|---|
196.7 ± 0.81 | Bouchoux and Salpin, 1999 | T = 302K; Re-evaluated thermokinetic parametric fitting by the authors using reference base GBs and PAs from Hunter and Lias, 1998; MM |
196.7 ± 0.81 | Bouchoux and Salpin, 1999 | T = 298K; MM |
Gas basicity at 298K
Gas basicity (review) (kcal/mol) | Reference | Comment |
---|---|---|
188.8 ± 0.36 | Bouchoux and Salpin, 1999 | T = 302K; Re-evaluated thermokinetic parametric fitting by the authors using reference base GBs and PAs from Hunter and Lias, 1998; MM |
188.8 ± 0.36 | Bouchoux and Salpin, 1999 | T = 298K; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.6191 ± 0.0004 | PE | Niu, Bai, et al., 1993 | LL |
9.614 ± 0.008 | PI | Vogt, Williamson, et al., 1978 | LLK |
9.61 ± 0.02 | PE | Vogt, Williamson, et al., 1978 | LLK |
9.63 ± 0.02 | PE | Hall, Maier, et al., 1977 | LLK |
9.64 | PE | Baker and Turner, 1969 | RDSH |
9.61 ± 0.02 | S | Price, Teegan, et al., 1951 | RDSH |
9.64 | PE | Bock, Hirabayashi, et al., 1981 | Vertical value; LLK |
9.60 | PE | Bock, Hirabayashi, et al., 1977 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHO+ | 16.1 ± 0.4 | CH | EI | Collin and Locht, 1970 | RDSH |
CH2+ | 13.729 ± 0.008 | CO | DER | McCulloh and Dibeler, 1976 | T = 0K; LLK |
CH2+ | 13.712 ± 0.008 | CO | PI | McCulloh and Dibeler, 1976 | T = 400K; LLK |
CH2+ | 13.8 ± 0.2 | CO | EI | Collin and Locht, 1970 | RDSH |
CO+ | 13.6 ± 0.3 | ? | EI | Collin and Locht, 1970 | RDSH |
C2HO+ | 14.9 ± 0.3 | H | EI | Collin and Locht, 1970 | RDSH |
De-protonation reactions
C2HO- + =
By formula: C2HO- + H+ = C2H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 364.8 ± 2.1 | kcal/mol | G+TS | Oakes, Jones, et al., 1983 | gas phase; Acid: ketene; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 357.8 ± 2.0 | kcal/mol | IMRB | Oakes, Jones, et al., 1983 | gas phase; Acid: ketene; value altered from reference due to change in acidity scale; B |
Ion clustering data
Go To: Top, Phase change 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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
(C2H3O- • 4294967295) +
= C2H3O-
By formula: (C2H3O- • 4294967295C2H2O) + C2H2O = C2H3O-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 61.5 ± 2.3 | kcal/mol | N/A | Bartmess, Scott, et al., 1979 | gas 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 |
By formula: F- + C2H2O = (F- • C2H2O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 35.3 | kcal/mol | ICR | Larson and McMahon, 1983 | gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 26.5 | cal/mol*K | N/A | Larson and McMahon, 1983 | gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 27.4 | kcal/mol | ICR | Larson and McMahon, 1983 | gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M |
References
Go To: Top, Phase change 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.
Reuben, 1969
Reuben, B.G.,
Vapor pressure of ketene,
J. Chem. Eng. Data, 1969, 14, 235. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Reuben, 1969, 2
Reuben, Bryan G.,
Vapor pressure of ketene,
J. Chem. Eng. Data, 1969, 14, 2, 235-236, https://doi.org/10.1021/je60041a008
. [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]
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]
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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy ΔfH(+) ion,0K Enthalpy of formation of positive ion at 0K ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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