Cyclobutanone
- Formula: C4H6O
- Molecular weight: 70.0898
- IUPAC Standard InChI: InChI=1S/C4H6O/c5-4-2-1-3-4/h1-3H2
- IUPAC Standard InChIKey: SHQSVMDWKBRBGB-UHFFFAOYSA-N
- CAS Registry Number: 1191-95-3
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction 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:
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 |
|---|---|---|---|---|---|
| ΔfH°gas | -91.6 | kJ/mol | Ccb | Rocek and Radkowsky, 1973 | ALS |
| ΔfH°gas | -101. ± 1. | kJ/mol | Ccb | Wolf, 1972 | ALS |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 38.53 | 50. | Thermodynamics Research Center, 1997 | p=1 bar. Selected entropies and heat capacities are different from statistical values calculated by [ Andreevskii D.N., 1976] within 1.7-4.5 J/mol*K for S(T) and 3.8-6.4 J/mol*K for Cp(T).; GT |
| 40.51 | 100. | ||
| 45.50 | 150. | ||
| 53.12 | 200. | ||
| 68.36 | 273.15 | ||
| 74.31 | 298.15 | ||
| 74.76 | 300. | ||
| 99.19 | 400. | ||
| 121.32 | 500. | ||
| 139.91 | 600. | ||
| 155.34 | 700. | ||
| 168.19 | 800. | ||
| 178.96 | 900. | ||
| 188.01 | 1000. | ||
| 195.66 | 1100. | ||
| 202.13 | 1200. | ||
| 207.6 | 1300. | ||
| 212.3 | 1400. | ||
| 216.3 | 1500. |
Condensed 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -131. | kJ/mol | Ccb | Rocek and Radkowsky, 1973 | |
| ΔfH°liquid | -139.5 ± 1.2 | kJ/mol | Ccb | Wolf, 1972 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -2300.7 ± 0.63 | kJ/mol | Ccb | Rocek and Radkowsky, 1973 | Corresponding ΔfHºliquid = -130.8 kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -2292.1 ± 1.2 | kJ/mol | Ccb | Wolf, 1972 | Corresponding ΔfHºliquid = -139.47 kJ/mol (simple calculation by NIST; no Washburn corrections) |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
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 |
|---|---|---|---|---|---|
| Tboil | 372.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
| Tboil | 1171.15 | K | N/A | Sieja, 1972 | Uncertainty assigned by TRC = 1.5 K; TRC |
| Tboil | 372.9 | K | N/A | Wolf, 1972, 2 | Uncertainty assigned by TRC = 0.5 K; TRC |
| Tboil | 372.2 | K | N/A | Roberts and Sauer, 1949 | Uncertainty assigned by TRC = 4. K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 38.3 | kJ/mol | V | Wiberg, Morgan, et al., 1994 | ALS |
| ΔvapH° | 38.4 | kJ/mol | A | Stephenson and Malanowski, 1987 | Based on data from 283. to 313. K.; AC |
| ΔvapH° | 38.2 ± 0.42 | kJ/mol | V | Wolf, 1972 | ALS |
| ΔvapH° | 38.2 ± 0.4 | kJ/mol | N/A | Wolf, 1972 | AC |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 37.7 | 322. | EB | Wiberg, Morgan, et al., 1994 | Based on data from 301. to 344. K.; AC |
| 36.3 | 332. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 317. to 380. K. See also Meyer and Hotz, 1976.; AC |
| 38.5 | 273. | N/A | Benson and Kistiakowsky, 1942 | Based on data from 249. to 298. K. See also Boublik, Fried, et al., 1984.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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| Temperature (K) | A | B | C | Reference | Comment |
|---|---|---|---|---|---|
| 249.09 to 298.39 | 5.00324 | 1740.994 | -19.419 | Benson and Kistiakowsky, 1942 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 10.8 | 220.5 | Gonthier-Vassal and Szwarc, 1998 | AC |
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 as indicated in comments:
B - John E. Bartmess
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
C4H5O- + =
By formula: C4H5O- + H+ = C4H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1536. ± 17. | kJ/mol | G+TS | Brickhouse and Squires, 1988 | gas phase; Between Me2C=NOH, EtCHO; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1502. ± 17. | kJ/mol | IMRB | Brickhouse and Squires, 1988 | gas phase; Between Me2C=NOH, EtCHO; B |
+
=
By formula: C4H6O + H2 = C4H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -67.91 ± 0.75 | kJ/mol | Chyd | Wiberg, Crocker, et al., 1991 | liquid phase; ALS |
| ΔrH° | -53. ± 1. | kJ/mol | Chyd | Wiberg, Crocker, et al., 1991 | gas phase; ALS |
+
=
+ 2
By formula: C6H12O2 + H2O = C4H6O + 2CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 25.4 ± 0.3 | kJ/mol | Cm | Wiberg, Morgan, et al., 1994 | liquid phase; ALS |
+ 2
=
+
By formula: C4H6O + 2CH4O = C6H12O2 + H2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -52.7 ± 1.7 | kJ/mol | Cm | Wiberg, Morgan, et al., 1994 | gas phase; ALS |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.
Rocek and Radkowsky, 1973
Rocek, J.; Radkowsky, A.E.,
Mechanism of the chromic acid oxidation of cyclobutanol,
J. Am. Chem. Soc., 1973, 95, 7123-7132. [all data]
Wolf, 1972
Wolf, G.,
Thermochemische Untersuchungen an cyclischen Ketonen,
Helv. Chim. Acta, 1972, 55, 1446-1459. [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]
Andreevskii D.N., 1976
Andreevskii D.N.,
Thermodynamic properties of C4-C6 cyclic ketones,
Zh. Prikl. Khim., 1976, 49, 1819-1823. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Sieja, 1972
Sieja, J.B.,
J. Chem. Eng. Data, 1972, 17, 108. [all data]
Wolf, 1972, 2
Wolf, G.,
Thermochemical studies of cyclic ketones,
Helv. Chim. Acta, 1972, 55, 1446. [all data]
Roberts and Sauer, 1949
Roberts, J.D.; Sauer, C.W.,
J. Am. Chem. Soc., 1949, 71, 3925. [all data]
Wiberg, Morgan, et al., 1994
Wiberg, K.B.; Morgan, K.M.; Maltz, H.,
Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria,
J. Am. Chem. Soc., 1994, 116, 11067-11077. [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]
Meyer and Hotz, 1976
Meyer, Edwin F.; Hotz, Carol A.,
Cohesive energies in polar organic liquids. 3. Cyclic ketones,
J. Chem. Eng. Data, 1976, 21, 3, 274-279, https://doi.org/10.1021/je60070a035
. [all data]
Benson and Kistiakowsky, 1942
Benson, S.W.; Kistiakowsky, G.B.,
The Photochemical Decomposition of Cyclic Ketones,
J. Am. Chem. Soc., 1942, 64, 1, 80-86, https://doi.org/10.1021/ja01253a021
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Gonthier-Vassal and Szwarc, 1998
Gonthier-Vassal, Anne; Szwarc, Henri,
Thermodynamic properties of cycloketones: A DSC study,
Thermochimica Acta, 1998, 320, 1-2, 141-154, https://doi.org/10.1016/S0040-6031(98)00409-2
. [all data]
Brickhouse and Squires, 1988
Brickhouse, M.D.; Squires, R.R.,
Gas Phase Bronsted vs. Lewis Acid-Base Reactions of 6,6-Dimethylfulvene. A Sensitive Probe of the Electronic Structures of Organic Anions,
J. Am. Chem. Soc., 1988, 110, 9, 2706, https://doi.org/10.1021/ja00217a002
. [all data]
Wiberg, Crocker, et al., 1991
Wiberg, K.B.; Crocker, L.S.; Morgan, K.M.,
Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups,
J. Am. Chem. Soc., 1991, 113, 3447-3450. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy 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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