3-Pentanone

Formula: C₅H₁₀O
Molecular weight: 86.1323
IUPAC Standard InChI: InChI=1S/C5H10O/c1-3-5(6)4-2/h3-4H2,1-2H3
IUPAC Standard InChIKey: FDPIMTJIUBPUKL-UHFFFAOYSA-N
CAS Registry Number: 96-22-0
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: Diethyl ketone; 1,3-Dimethylacetone; DEK; Ethyl ketone; Metacetone; Methacetone; Propione; (C2H5)2CO; Ethyl propionyl; Pentan-3-one; Diethylcetone; Pentanone-3; UN 1156; Dimethylacetone; NSC 8653
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References, Notes

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
Δ_fH°_gas	-60.6 ± 0.2	kcal/mol	Ccb	Gerasimov and Gubareva, 1985	The hf_gas reanalyzed by ALS; ALS
Δ_fH°_gas	-61.65 ± 0.20	kcal/mol	Ccb	Harrop, Head, et al., 1970	ALS
Δ_fH°_gas	-62.25 ± 0.39	kcal/mol	Eqk	Buckley and Herington, 1965	Reanalyzed by Cox and Pilcher, 1970, Original value = -61.82 kcal/mol; ALS

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
34.969	364.15	Hales J.L., 1967	Experimental data [ Vilcu R., 1975] differ substantially from data selected here. Their correctness seems to be doubtful (see [ Kabo G.J., 1995]).; GT
36.181	383.15
37.469	403.15
38.750	423.15
40.320	448.15
41.859	473.15

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References, Notes

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	-70.87 ± 0.20	kcal/mol	Ccb	Harrop, Head, et al., 1970	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-742.0 ± 0.2	kcal/mol	Ccb	Gerasimov and Gubareva, 1985	The hf_gas reanalyzed by ALS; Corresponding Δ_fHº_liquid = -69.79 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-740.96 ± 0.24	kcal/mol	Ccb	Harrop, Head, et al., 1970	Corresponding Δ_fHº_liquid = -70.868 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	63.58	cal/mol*K	N/A	Andon, Counsell, et al., 1968	DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
46.94	298.15	Baglay, Gurariy, et al., 1988	T = 270 to 340 K. Unsmoothed experimental datum.; DH
46.77	298.15	Baglai, Baev, et al., 1984	T = 273 to 334 K. Cp(liq) = -1.85557 + 0.025782T - 4.0x10-5T2 kJ/kg*K (273 to 335 K).; DH
45.483	298.15	Grolier and Benson, 1984	DH
45.41	298.15	Saluja, Peacock, et al., 1979	DH
47.97	298.15	Harrop, Head, et al., 1970	DH
45.63	298.15	Andon, Counsell, et al., 1968	T = 10 to 320 K.; DH

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes

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

View reactions leading to C₅H₁₀O⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	9.31 ± 0.02	eV	N/A	N/A	L
Quantity	Value	Units	Method	Reference	Comment
Proton affinity (review)	200.0	kcal/mol	N/A	Hunter and Lias, 1998	HL
Quantity	Value	Units	Method	Reference	Comment
Gas basicity	193.	kcal/mol	N/A	Hunter and Lias, 1998	HL

Gas basicity at 298K

Gas basicity (review) (kcal/mol)	Reference	Comment
192.1 ± 0.07	Decouzon, Gal, et al., 1996	T = 338K; MM
191.8	Decouzon, Gal, et al., 1996	T = T(eff) = 430K; MM

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.31	PI	Traeger, 1985	LBLHLM
9.30	EI	Holmes, Fingas, et al., 1981	LLK
9.22 ± 0.02	PE	Ashmore and Burgess, 1978	LLK
9.309 ± 0.005	PE	Hernandez, Masclet, et al., 1977	LLK
9.31 ± 0.01	PE	Mouvier and Hernandez, 1975	LLK
9.37 ± 0.03	EI	Mouvier and Hernandez, 1975	LLK
9.31 ± 0.02	PE	Cocksey, Eland, et al., 1971	LLK
9.32 ± 0.01	PI	Watanabe, Nakayama, et al., 1962	RDSH

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₂H₅⁺	13.04	?	EI	Potzinger and Bunau, 1969	RDSH
C₃H₅O⁺	9.81	C₂H₅	PI	Traeger, 1985	LBLHLM
C₃H₅O⁺	10.10	?	EI	Mouvier and Hernandez, 1975	LLK

De-protonation reactions

C₅H₉O^- + = 3-Pentanone

By formula: C₅H₉O^- + H⁺ = C₅H₁₀O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	368.5 ± 2.2	kcal/mol	G+TS	Cumming and Kebarle, 1978	gas phase; B
Δ_rH°	362.8 ± 2.3	kcal/mol	D-EA	Zimmerman, Reed, et al., 1977	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	361.4 ± 2.0	kcal/mol	IMRE	Cumming and Kebarle, 1978	gas phase; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, Notes

Gerasimov and Gubareva, 1985
Gerasimov, P.A.; Gubareva, A.I., Physical chemical properties of vitamin A precursor ketones, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1985, 28, 106-109. [all data]

Harrop, Head, et al., 1970
Harrop, D.; Head, A.J.; Lewis, G.B., Thermodynamic properties of organic oxygen compounds. 22. Enthalpies of combustion of some aliphatic ketones, J. Chem. Thermodyn., 1970, 2, 203-210. [all data]

Buckley and Herington, 1965
Buckley, E.; Herington, E.F.G., Equilibria in some secondary alcohol + hydrogen + ketone systems, Trans. Faraday Soc., 1965, 61, 1618-1625. [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]

Hales J.L., 1967
Hales J.L., Thermodynamic properties of organic oxygen compounds. Part 18. Vapor heat capacities and heats of vaporization of ethyl ketone, ethyl propyl ketone, methyl isopropyl ketone, and methyl phenyl ether, Trans. Faraday Soc., 1967, 63, 1876-1879. [all data]

Vilcu R., 1975
Vilcu R., Determination of heat capacities of some alcohols and ketones in vapor phase, Rev. Roum. Chim., 1975, 20, 603-609. [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]

Andon, Counsell, et al., 1968
Andon, R.J.L.; Counsell, J.F.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XX. The low-temperature heat capacity and entropy of C₄ and C₅ ketones, J. Chem. Soc. A, 1968, 1894-1897. [all data]

Baglay, Gurariy, et al., 1988
Baglay, A.K.; Gurariy, L.L.; Kuleshov, G.G., Physical properties of compounds used in vitamin synthesis, J. Chem. Eng. Data, 1988, 33, 512-518. [all data]

Baglai, Baev, et al., 1984
Baglai, A.K.; Baev, A.A.; Belousov, V.P.; Beregovykh, V.V.; Grushenko, M.M.; Gurarii, L.L.; Konstantinov, S.G.; Kostyushko, Yu.L.; Kuleshov, G.G.; Pasechnik, N.I.; Petrashkevich, R.I.; Podkovyrov, A.I.; Sitnov, A.A.; Shishko, M.A.; Shulgin, I.L., Investigation of the physico-chemical characteristics of substances utilized in the synthesis of vitamins A and E, Khim. Farm. Zhur., 1984, 18, 1013-1019. [all data]

Grolier and Benson, 1984
Grolier, J.-P.E.; Benson, G.C., Thermodynamic properties of binary mixtures containing ketones. VIII. Heat capacities and volumes of some n-alkanone + n-alkane mixtures at 298.15 K, Can. J. Chem., 1984, 62, 949-953. [all data]

Saluja, Peacock, et al., 1979
Saluja, P.P.S.; Peacock, L.A.; Fuchs, R., Enthalpies of interaction of aliphatic ketones with polar and nonpolar solvents, J. Am. Chem. Soc., 1979, 101, 1958-1962. [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]

Decouzon, Gal, et al., 1996
Decouzon, M.; Gal, J.E.; Herreros, M.; Marai, P.C.; Murrell, J.; Todd, J.F.J., On the Use of the Kinetic Method for the Determination of Proton Affinities by Fourier-Transfrom Ion Cyclotron Resonance Mass Spectrometry, Rapid. Comm. Mass Spectrom., 1996, 10, 242. [all data]

Traeger, 1985
Traeger, J.C., Heat of formation for the propanoyl cation by photoionization mass spectrometry, Org. Mass Spectrom., 1985, 20, 223. [all data]

Holmes, Fingas, et al., 1981
Holmes, J.L.; Fingas, M.; Lossing, F.P., Towards a general scheme for estimating the heats of formation of organic ions in the gas phase. Part I. Odd-electron cations, Can. J. Chem., 1981, 59, 80. [all data]

Ashmore and Burgess, 1978
Ashmore, F.S.; Burgess, A.R., Photoelectron spectra of the unbranched C₅-C₇ alkenes, aldehydes and ketones, J. Chem. Soc. Faraday Trans. 2, 1978, 74, 734. [all data]

Hernandez, Masclet, et al., 1977
Hernandez, R.; Masclet, P.; Mouvier, G., Spectroscopie de photoelectrons d'aldehydes et de cetones aliphatiques, J. Electron Spectrosc. Relat. Phenom., 1977, 10, 333. [all data]

Mouvier and Hernandez, 1975
Mouvier, G.; Hernandez, R., Ionisation and appearance potentials of alkylketones, Org. Mass Spectrom., 1975, 10, 958. [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]

Potzinger and Bunau, 1969
Potzinger, P.; Bunau, G.v., Empirische Beruksichtigung von Uberschussenergien bei der Auftrittspotentialbestimmung, Ber. Bunsen-Ges. Phys. Chem., 1969, 73, 466. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Zimmerman, Reed, et al., 1977
Zimmerman, A.H.; Reed, K.J.; Brauman, J.I., Photodetachment of electrons from enolate anions. Gas phase electron affinities of enolate radicals, J. Am. Chem. Soc., 1977, 99, 7203. [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:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
IE (evaluated)	Recommended ionization energy
S°_liquid	Entropy of liquid at standard conditions
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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