Cyclohexanone
- Formula: C6H10O
- Molecular weight: 98.1430
- IUPAC Standard InChIKey: JHIVVAPYMSGYDF-UHFFFAOYSA-N
- CAS Registry Number: 108-94-1
- 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: Anon; Anone; Hexanon; Hytrol O; Nadone; Pimelic ketone; Pimelin ketone; Sextone; Ketohexamethylene; Cicloesanone; Cyclohexanon; Cykloheksanon; NCI-C55005; Rcra waste number U057; UN 1915; Cyclohexyl ketone; NSC 5711
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Gas phase thermochemistry data
Go To: Top, Gas phase ion energetics data, IR 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 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 | -55.23 ± 0.21 | kcal/mol | Cm | Wiberg, Crocker, et al., 1991 | ALS |
ΔfH°gas | -53.94 | kcal/mol | Eqk | Kabo, Yursha, et al., 1988 | ALS |
ΔfH°gas | -54.43 ± 0.45 | kcal/mol | Ccb | Wolf, 1972 | ALS |
ΔfH°gas | -54.09 | kcal/mol | Ccb | Sellers and Sunner, 1962 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 80.194 | cal/mol*K | N/A | Kabo G.J., 1988 | GT |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
28.934 | 298.15 | Kabo G.J., 1988 | Selected thermodynamic functions are in better agreement with experimental values of S(298.15 K) and Cp(T) than statistical values calculated by [ Thermodynamics Research Center, 1997, Andreevskii D.N., 1976]. Maximum discrepancies with functions given in [ Thermodynamics Research Center, 1997] amount to 2.5 and 5.0 J/mol*K for S(T) and Cp(T), respectively. Discrepancies with data [ Andreevskii D.N., 1976] reach 11 and 8 J/mol*K for S(T) and Cp(T), respectively.; GT |
29.132 | 300. | ||
38.690 | 400. | ||
46.938 | 500. | ||
53.834 | 600. | ||
59.577 | 700. | ||
64.405 | 800. | ||
68.478 | 900. | ||
71.955 | 1000. |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
37.094 | 385. | Shvaro O.V., 1987 | The experimental values of Cp(T) obtained by [ Vilcu R., 1975] seem to be not enough reliable in view of the comparison of experimental heat capacities of some alcohols and ketones measured by these authors (see [ Kabo G.J., 1995]).; GT |
38.497 | 400. | ||
40.387 | 420. | ||
42.020 | 440. | ||
43.893 | 460. | ||
45.454 | 480. |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, IR Spectrum, 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
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C6H10O+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.16 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 201.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 193.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.0033 | EFD | Desfrancois, Abdoul-Carime, et al., 1994 | EA: 3.3 meV. Dipole-bound state.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.18 | PE | Loudet, Grimaud, et al., 1976 | LLK |
9.5 ± 0.2 | EI | Fortin, Forest, et al., 1973 | LLK |
9.16 ± 0.01 | PE | Cocksey, Eland, et al., 1971 | LLK |
9.14 ± 0.01 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
9.14 ± 0.03 | PI | Vilesov, 1960 | RDSH |
9.29 | PE | Spanka and Rademacher, 1986 | Vertical value; LBLHLM |
9.18 | PE | Kovac and Klasinc, 1978 | Vertical value; LLK |
9.28 | PE | Hentrich, Gunkel, et al., 1974 | Vertical value; LLK |
9.14 ± 0.02 | PE | Chadwick, Frost, et al., 1971 | Vertical value; LLK |
De-protonation reactions
C6H9O- + =
By formula: C6H9O- + H+ = C6H10O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 366.4 ± 2.0 | kcal/mol | D-EA | Brinkman, Berger, et al., 1993 | gas phase; B |
ΔrH° | 365.8 ± 2.3 | kcal/mol | D-EA | Zimmerman, Jackson, et al., 1978 | gas phase; B |
ΔrH° | 369.0 ± 4.2 | kcal/mol | G+TS | Brickhouse and Squires, 1988 | gas phase; Between acetone, Me2C=NOH; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 358.7 ± 2.3 | kcal/mol | H-TS | Brinkman, Berger, et al., 1993 | gas phase; B |
ΔrG° | 358.0 ± 2.6 | kcal/mol | H-TS | Zimmerman, Jackson, et al., 1978 | gas phase; B |
ΔrG° | 361.2 ± 4.0 | kcal/mol | IMRB | Brickhouse and Squires, 1988 | gas phase; Between acetone, Me2C=NOH; B |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Kabo, Yursha, et al., 1988
Kabo, G.J.; Yursha, I.A.; Frenkel, M.L.; Poleshchuk, P.A.; Fedoseenko, V.I.; Ladutko, A.I.,
Thermodynamic properties of cyclohexanol and cyclohexanone,
J. Chem. Thermodyn., 1988, 20, 429-437. [all data]
Wolf, 1972
Wolf, G.,
Thermochemische Untersuchungen an cyclischen Ketonen,
Helv. Chim. Acta, 1972, 55, 1446-1459. [all data]
Sellers and Sunner, 1962
Sellers, P.; Sunner, S.,
Heats of combustion of cyclic ketones and alcohols,
Acta Chem. Scand., 1962, 16, 46-52. [all data]
Kabo G.J., 1988
Kabo G.J.,
Thermodynamic properties of cyclohexanol and cyclohexanone,
J. Chem. Thermodyn., 1988, 20, 429-437. [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]
Shvaro O.V., 1987
Shvaro O.V.,
Thermodynamic properties of cyclopentanone and cyclohexanone,
Inzh.-Fiz. Zh., 1987, 52, 807-812. [all data]
Vilcu R., 1975
Vilcu R.,
Heat capacity of cyclohexanone and 4-methylcyclohexanone in the vapor phase,
Rev. Chim. (Bucharest), 1975, 26, 129-131. [all data]
Kabo G.J., 1995
Kabo G.J.,
Thermodynamic properties, conformation, and phase transitions of cyclopentanol,
J. Chem. Thermodyn., 1995, 27, 953-967. [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]
Loudet, Grimaud, et al., 1976
Loudet, M.; Grimaud, M.; Metras, F.; Pfister-Guillouzo, G.,
Interactions intramoleculaires en serie cyclohexanique partie II. Spectres photoelectroniques de chloro-2-cyclohexanones,
J. Mol. Struct., 1976, 35, 213. [all data]
Fortin, Forest, et al., 1973
Fortin, C.J.; Forest, M.; Vaziri, C.; Gravel, D.; Rousseau, Y.,
Spectrometrie de masse des cyclohexanones gem-diphenylees. I. Localisation de la charge positive,
Can. J. Chem., 1973, 51, 3445. [all data]
Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J.,
The effect of alkyl substitution on ionisation potential,
J. Chem. Soc., 1971, (B), 790. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Vilesov, 1960
Vilesov, F.I.,
The photoionization of vapors of compounds whose molecules contain carbonyl groups,
Dokl. Phys. Chem., 1960, 132, 521, In original 1332. [all data]
Spanka and Rademacher, 1986
Spanka, G.; Rademacher, P.,
Transannular interactions in difunctional medium rings. 1. n/π Interactions in cyclic amino ketones and aminoalkenes studied by photoelectron spectroscopy,
J. Org. Chem., 1986, 51, 592. [all data]
Kovac and Klasinc, 1978
Kovac, B.; Klasinc, L.,
Photoelectron spectroscopy of adamantane and some adamantanones,
Croat. Chem. Acta, 1978, 51, 55. [all data]
Hentrich, Gunkel, et al., 1974
Hentrich, G.; Gunkel, E.; Klessinger, M.,
Photoelektronenspektren organischer verbindungen. 4. Photoelektronenspektren ungesattigter carbonylverbindungen,
J. Mol. Struct., 1974, 21, 231. [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]
Brinkman, Berger, et al., 1993
Brinkman, E.A.; Berger, S.; Marks, J.; Brauman, J.I.,
Molecular Rotation and the Observation of Dipole-Bound States of Anions,
J. Chem. Phys., 1993, 99, 10, 7586, https://doi.org/10.1063/1.465688
. [all data]
Zimmerman, Jackson, et al., 1978
Zimmerman, A.H.; Jackson, R.L.; Janousek, B.K.; Brauman, J.J.,
Electron photodetachment from cyclic enolate anions in the gas phase: Electron affinities of cyclic enolate radicals,
J. Am. Chem. Soc., 1978, 100, 4674. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas EA Electron affinity IE (evaluated) Recommended ionization energy S°gas Entropy of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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