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
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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 |
|---|---|---|---|---|---|
| ΔfH°gas | -21.9 | kcal/mol | Ccb | Rocek and Radkowsky, 1973 | ALS |
| ΔfH°gas | -24.2 ± 0.3 | kcal/mol | Ccb | Wolf, 1972 | ALS |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 9.209 | 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 |
| 9.682 | 100. | ||
| 10.87 | 150. | ||
| 12.70 | 200. | ||
| 16.34 | 273.15 | ||
| 17.76 | 298.15 | ||
| 17.87 | 300. | ||
| 23.71 | 400. | ||
| 28.996 | 500. | ||
| 33.439 | 600. | ||
| 37.127 | 700. | ||
| 40.198 | 800. | ||
| 42.772 | 900. | ||
| 44.935 | 1000. | ||
| 46.764 | 1100. | ||
| 48.310 | 1200. | ||
| 49.62 | 1300. | ||
| 50.74 | 1400. | ||
| 51.70 | 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 | -31.3 | kcal/mol | Ccb | Rocek and Radkowsky, 1973 | |
| ΔfH°liquid | -33.34 ± 0.28 | kcal/mol | Ccb | Wolf, 1972 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -549.89 ± 0.15 | kcal/mol | Ccb | Rocek and Radkowsky, 1973 | Corresponding ΔfHºliquid = -31.26 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -547.82 ± 0.28 | kcal/mol | Ccb | Wolf, 1972 | Corresponding ΔfHºliquid = -33.334 kcal/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° | 9.15 | kcal/mol | V | Wiberg, Morgan, et al., 1994 | ALS |
| ΔvapH° | 9.18 | kcal/mol | A | Stephenson and Malanowski, 1987 | Based on data from 283. to 313. K.; AC |
| ΔvapH° | 9.14 ± 0.10 | kcal/mol | V | Wolf, 1972 | ALS |
| ΔvapH° | 9.13 ± 0.1 | kcal/mol | N/A | Wolf, 1972 | AC |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 9.01 | 322. | EB | Wiberg, Morgan, et al., 1994 | Based on data from 301. to 344. K.; AC |
| 8.68 | 332. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 317. to 380. K. See also Meyer and Hotz, 1976.; AC |
| 9.20 | 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 (atm)
T = temperature (K)
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| Temperature (K) | A | B | C | Reference | Comment |
|---|---|---|---|---|---|
| 249.09 to 298.39 | 4.99753 | 1740.994 | -19.419 | Benson and Kistiakowsky, 1942 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 2.58 | 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° | 367.1 ± 4.1 | kcal/mol | G+TS | Brickhouse and Squires, 1988 | gas phase; Between Me2C=NOH, EtCHO; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 359.0 ± 4.0 | kcal/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° | -16.23 ± 0.18 | kcal/mol | Chyd | Wiberg, Crocker, et al., 1991 | liquid phase; ALS |
| ΔrH° | -12.7 ± 0.3 | kcal/mol | Chyd | Wiberg, Crocker, et al., 1991 | gas phase; ALS |
+
=
+ 2
By formula: C6H12O2 + H2O = C4H6O + 2CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 6.07 ± 0.07 | kcal/mol | Cm | Wiberg, Morgan, et al., 1994 | liquid phase; ALS |
+ 2
=
+
By formula: C4H6O + 2CH4O = C6H12O2 + H2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -12.6 ± 0.41 | kcal/mol | Cm | Wiberg, Morgan, et al., 1994 | gas phase; ALS |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, UV/Visible spectrum, 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
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Additional Data
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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. |
|---|---|
| Origin | NIST Mass Spectrometry Data Center, 1990. |
| NIST MS number | 118863 |
UV/Visible spectrum
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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Download spectrum in JCAMP-DX format.
| Source | missing citation |
|---|---|
| Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
| Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
| Source reference | RAS UV No. 1408 |
| Instrument | Cary 14R |
| Melting point | -50.9 |
| Boiling point | 99 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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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