Cyclopentanone

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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
Δfgas-197.4 ± 1.3kJ/molCmWiberg, Crocker, et al., 1991ALS
Δfgas-194.8 ± 1.7kJ/molCcbWolf, 1972ALS
Δfgas-193.0 ± 1.8kJ/molCcbSellers and Sunner, 1962Reanalyzed by Cox and Pilcher, 1970, Original value = -193.8 kJ/mol; ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
38.3150.Thermodynamics Research Center, 1997p=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
45.17100.
53.92150.
65.64200.
87.22273.15
95.33298.15
95.93300.
128.42400.
157.31500.
181.43600.
201.42700.
218.14800.
232.24900.
244.211000.
254.411100.
263.11200.
270.61300.
277.11400.
282.61500.

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
116.90360.Shvaro O.V., 1987GT
121.16375.
128.03400.
133.86420.
139.31440.
144.04460.
149.22480.

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
Δfliquid-240.2 ± 1.3kJ/molCmWiberg, Crocker, et al., 1991 
Δfliquid-237.4 ± 1.7kJ/molCcbWolf, 1972 
Δfliquid-236.5kJ/molCcbSellers and Sunner, 1962 
Quantity Value Units Method Reference Comment
Δcliquid-2873.5 ± 1.6kJ/molCcbWolf, 1972Corresponding Δfliquid = -237.35 kJ/mol (simple calculation by NIST; no Washburn corrections)
Δcliquid-2874.0 ± 0.92kJ/molCcbSellers and Sunner, 1962Corresponding Δfliquid = -236.9 kJ/mol (simple calculation by NIST; no Washburn corrections)
Δcliquid-2870. ± 0.8kJ/molCcbSkuratov, Kozina, et al., 1957At 20C; Corresponding Δfliquid = -241. kJ/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 ± 0.01eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)823.7kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity794.0kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.00169EFDDesfrancois, Abdoul-Carime, et al., 1994EA: 1.7 meV. Dipole-bound state.; B

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
828. ± 4.Morlender-Vais and Holmes, 2001MM

Ionization energy determinations

IE (eV) Method Reference Comment
9.28 ± 0.01PECocksey, Eland, et al., 1971LLK
9.25 ± 0.02PEChadwick, Frost, et al., 1971LLK
9.26 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
9.42 ± 0.03PIVilesov, 1960RDSH
9.3PEBieri, Asbrink, et al., 1982Vertical value; LBLHLM
9.10PEKovac and Klasinc, 1978Vertical value; LLK
9.28PEGerson, Worley, et al., 1978Vertical value; LLK
9.28PEHentrich, Gunkel, et al., 1974Vertical value; LLK
9.25 ± 0.02PEChadwick, Frost, et al., 1971, 2Vertical value; LLK

De-protonation reactions

C5H7O- + Hydrogen cation = Cyclopentanone

By formula: C5H7O- + H+ = C5H8O

Quantity Value Units Method Reference Comment
Δr1540. ± 18.kJ/molG+TSBrickhouse and Squires, 1988gas phase; B
Quantity Value Units Method Reference Comment
Δr1507. ± 17.kJ/molIMRBBrickhouse and Squires, 1988gas 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