Cyclopentanone
- Formula: C5H8O
- Molecular weight: 84.1164
- IUPAC Standard InChI: InChI=1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2
- IUPAC Standard InChIKey: BGTOWKSIORTVQH-UHFFFAOYSA-N
- CAS Registry Number: 120-92-3
- 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: Adipic ketone; Adipinketon; Dumasin; Ketocyclopentane; Ketopentamethylene; UN 2245; NSC 4122
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry 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:
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 | -47.19 ± 0.30 | kcal/mol | Cm | Wiberg, Crocker, et al., 1991 | ALS |
| ΔfH°gas | -46.55 ± 0.41 | kcal/mol | Ccb | Wolf, 1972 | ALS |
| ΔfH°gas | -46.12 ± 0.44 | kcal/mol | Ccb | Sellers and Sunner, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = -46.31 kcal/mol; ALS |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 9.156 | 50. | Thermodynamics Research Center, 1997 | p=1 bar. Selected entropies and heat capacities agree within 2 J/mol*K with statistical values calculated by [ Shvaro O.V., 1987] except for S(1000 K) which value is about 6 J/mol*K lower than that of [ Thermodynamics Research Center, 1997]. Discrepancies with statistical calculation of [ Andreevskii D.N., 1976] amount to 4-12 J/mol*K for S(T) and 3-8 J/mol*K for Cp(T).; GT |
| 10.80 | 100. | ||
| 12.89 | 150. | ||
| 15.69 | 200. | ||
| 20.85 | 273.15 | ||
| 22.78 | 298.15 | ||
| 22.93 | 300. | ||
| 30.693 | 400. | ||
| 37.598 | 500. | ||
| 43.363 | 600. | ||
| 48.141 | 700. | ||
| 52.137 | 800. | ||
| 55.507 | 900. | ||
| 58.368 | 1000. | ||
| 60.805 | 1100. | ||
| 62.88 | 1200. | ||
| 64.67 | 1300. | ||
| 66.23 | 1400. | ||
| 67.54 | 1500. |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 27.940 | 360. | Shvaro O.V., 1987 | GT |
| 28.958 | 375. | ||
| 30.600 | 400. | ||
| 31.993 | 420. | ||
| 33.296 | 440. | ||
| 34.426 | 460. | ||
| 35.664 | 480. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -57.40 ± 0.30 | kcal/mol | Cm | Wiberg, Crocker, et al., 1991 | |
| ΔfH°liquid | -56.74 ± 0.40 | kcal/mol | Ccb | Wolf, 1972 | |
| ΔfH°liquid | -56.52 | kcal/mol | Ccb | Sellers and Sunner, 1962 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -686.79 ± 0.39 | kcal/mol | Ccb | Wolf, 1972 | Corresponding ΔfHºliquid = -56.728 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -686.91 ± 0.22 | kcal/mol | Ccb | Sellers and Sunner, 1962 | Corresponding ΔfHºliquid = -56.61 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -685.9 ± 0.2 | kcal/mol | Ccb | Skuratov, Kozina, et al., 1957 | At 20C; Corresponding ΔfHºliquid = -57.6 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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 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)
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 9.26 ± 0.01 | eV | N/A | N/A | L |
| Quantity | Value | Units | Method | Reference | Comment |
| Proton affinity (review) | 196.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 189.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 0.00169 | EFD | Desfrancois, Abdoul-Carime, et al., 1994 | EA: 1.7 meV. Dipole-bound state.; B |
Proton affinity at 298K
| Proton affinity (kcal/mol) | Reference | Comment |
|---|---|---|
| 198. ± 1. | Morlender-Vais and Holmes, 2001 | MM |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.28 ± 0.01 | PE | Cocksey, Eland, et al., 1971 | LLK |
| 9.25 ± 0.02 | PE | Chadwick, Frost, et al., 1971 | LLK |
| 9.26 ± 0.01 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
| 9.42 ± 0.03 | PI | Vilesov, 1960 | RDSH |
| 9.3 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
| 9.10 | PE | Kovac and Klasinc, 1978 | Vertical value; LLK |
| 9.28 | PE | Gerson, Worley, et al., 1978 | Vertical value; LLK |
| 9.28 | PE | Hentrich, Gunkel, et al., 1974 | Vertical value; LLK |
| 9.25 ± 0.02 | PE | Chadwick, Frost, et al., 1971, 2 | Vertical value; LLK |
De-protonation reactions
C5H7O- + =
By formula: C5H7O- + H+ = C5H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 368.0 ± 4.2 | kcal/mol | G+TS | Brickhouse and Squires, 1988 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 360.3 ± 4.0 | kcal/mol | IMRB | Brickhouse and Squires, 1988 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, 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]
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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]
Shvaro O.V., 1987
Shvaro O.V.,
Thermodynamic properties of cyclopentanone and cyclohexanone,
Inzh.-Fiz. Zh., 1987, 52, 807-812. [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]
Skuratov, Kozina, et al., 1957
Skuratov, S.M.; Kozina, M.L.; Shteher, S.M.; Varushyenko, R.M.,
The heats of combustion of several purified compounds,
Thermochem. Bull. (Moscow State Univ.), March, 1957, 36-37. [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]
Morlender-Vais and Holmes, 2001
Morlender-Vais, N.; Holmes, J.L.,
Proton affinities of two weakly bidentate molecules: 1,2-Dimethoxyethane and methoxyacetone,
Int. J. Mass Spectrom., 2001, 210/211, 147. [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]
Chadwick, Frost, et al., 1971
Chadwick, D.; Frost, D.C.; Weiler, L.,
Photoelectron spectra of cyclopentanone and cyclopentenones,
J. Am. Chem. Soc., 1971, 93, 4320. [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]
Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W.,
30.4-nm He(II) photoelectron spectra of organic molecules,
J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [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]
Gerson, Worley, et al., 1978
Gerson, S.H.; Worley, S.D.; Bodor, N.; Kaminski, J.J.; Flechtner, T.W.,
The photoelectron spectra of some heterocyclic compounds which contain N, O, Cl, and Br,
J. Electron Spectrosc. Relat. Phenom., 1978, 13, 421. [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, 2
Chadwick, D.; Frost, D.C.; Weiler, L.,
The photoelectron spectra of cyclic ketones,
Tetrahedron Lett., 1971, 47, 4543. [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, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas EA Electron affinity IE (evaluated) Recommended ionization energy 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 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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