Cyclobutanone
- Formula: C4H6O
- Molecular weight: 70.0898
- 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 | -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 |
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 |
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 |
Gas phase ion energetics 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 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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C4H6O+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.354 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 802.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 772.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.000999 | EFD | Desfrancois, Abdoul-Carime, et al., 1994 | EA: 1.0 meV. Dipole-bound state.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.4 ± 0.1 | EI | Rothgery, Holt, et al., 1975 | LLK |
9.6 ± 0.1 | EI | Branton and Pua, 1973 | LLK |
9.354 | S | Whitlock and Duncan, 1971 | LLK |
9.61 ± 0.02 | PE | Chadwick, Frost, et al., 1971 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H2O+ | 10.53 ± 0.15 | C2H4 | EI | Branton and Pua, 1973 | LLK |
C3H6+ | 9.85 ± 0.15 | CO | EI | Branton and Pua, 1973 | LLK |
De-protonation 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 |
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)
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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: 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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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 |
Gas Chromatography
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Polydimethyl siloxane | 105. | 642. | Tello, Lebron-Aguilar, et al., 2009 | |
Capillary | Polydimethyl siloxane | 75. | 639. | Tello, Lebron-Aguilar, et al., 2009 | |
Capillary | Polydimethyl siloxane | 90. | 641. | Tello, Lebron-Aguilar, et al., 2009 | |
Capillary | Methyl Silicone | 100. | 641. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 | |
Capillary | Methyl Silicone | 120. | 645. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 | |
Capillary | Methyl Silicone | 140. | 647. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 | |
Capillary | Methyl Silicone | 80. | 639. | Lebrón-Aguilar, Quintanilla-López, et al., 2007 |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 633. | Zenkevich, 1996 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, 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]
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]
Desfrancois, Abdoul-Carime, et al., 1994
Desfrancois, C.; Abdoul-Carime, H.; Khelifa, N.; Schermann, J.P.,
Fork 1/r to 1/r2 Potentials: Electron Exchange between Rydberg Atoms and Polar Molecules,
Phys. Rev. Lett., 1994, 73, 18, 2436, https://doi.org/10.1103/PhysRevLett.73.2436
. [all data]
Rothgery, Holt, et al., 1975
Rothgery, E.F.; Holt, J.; McGee, H.A., Jr.,
Cryochemical synthesis and molecular energetics of cyclopropanone and some related compounds,
J. Am. Chem. Soc., 1975, 97, 4971. [all data]
Branton and Pua, 1973
Branton, G.R.; Pua, C.K.N.,
Low energy electron impact ionization and fragmentation-cyclobutanone,
Can. J. Chem., 1973, 51, 624. [all data]
Whitlock and Duncan, 1971
Whitlock, R.F.; Duncan, A.B.F.,
Electronic spectrum of cyclobutanone,
J. Chem. Phys., 1971, 55, 218. [all data]
Chadwick, Frost, et al., 1971
Chadwick, D.; Frost, D.C.; Weiler, L.,
The photoelectron spectra of cyclic ketones,
Tetrahedron Lett., 1971, 47, 4543. [all data]
Tello, Lebron-Aguilar, et al., 2009
Tello, A.M.; Lebron-Aguilar, R.; Quintanilla-Lopez, J.E.; Santiuste, J.M.,
Isothermal retention indices on poly93-cyanopropylmethyl)siloxane stationary phases,
J. Chromatogr. A, 2009, 1216, 10, 1630-1639, https://doi.org/10.1016/j.chroma.2008.10.025
. [all data]
Lebrón-Aguilar, Quintanilla-López, et al., 2007
Lebrón-Aguilar, R.; Quintanilla-López, J.E.; Tello, A.M.; Santiuste, J.M.,
Isothermal retention indices on poly (3,3,3-trifluoropropylmethylsiloxane) stationary phases,
J. Chromatogr. A, 2007, 1160, 1-2, 276-288, https://doi.org/10.1016/j.chroma.2007.05.025
. [all data]
Zenkevich, 1996
Zenkevich, I.G.,
Informational Maitenance of Gas Chromatographic Identification of Organic Compounds in Ecoanalytical Investigations,
Z. Anal. Chem., 1996, 51, 11, 1140-1148. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas EA Electron affinity IE (evaluated) Recommended ionization energy 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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