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3-Pentanone

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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
Deltafgas-253.4 ± 0.9kJ/molCcbGerasimov and Gubareva, 1985The hf_gas reanalyzed by ALS; ALS
Deltafgas-257.95 ± 0.84kJ/molCcbHarrop, Head, et al., 1970ALS
Deltafgas-260.5 ± 1.6kJ/molEqkBuckley and Herington, 1965Reanalyzed by Cox and Pilcher, 1970, Original value = -258.7 kJ/mol; ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
146.31364.15Hales J.L., 1967Experimental data [ Vilcu R., 1975] differ substantially from data selected here. Their correctness seems to be doubtful (see [ Kabo G.J., 1995]).; GT
151.38383.15
156.77403.15
162.13423.15
168.70448.15
175.14473.15

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Reaction 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 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
Deltafliquid-296.51 ± 0.83kJ/molCcbHarrop, Head, et al., 1970ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3104.7 ± 0.9kJ/molCcbGerasimov and Gubareva, 1985The hf_gas reanalyzed by ALS; Corresponding «DELTA»fliquid = -292.0 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-3100.2 ± 1.0kJ/molCcbHarrop, Head, et al., 1970Corresponding «DELTA»fliquid = -296.51 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid266.0J/mol*KN/AAndon, Counsell, et al., 1968DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
196.4298.15Baglay, Gurariy, et al., 1988T = 270 to 340 K. Unsmoothed experimental datum.; DH
195.7298.15Baglai, Baev, et al., 1984T = 273 to 334 K. Cp(liq) = -1.85557 + 0.025782T - 4.0x10-5T2 kJ/kg*K (273 to 335 K).; DH
190.30298.15Grolier and Benson, 1984DH
190.0298.15Saluja, Peacock, et al., 1979DH
200.7298.15Harrop, Head, et al., 1970DH
190.9298.15Andon, Counsell, et al., 1968T = 10 to 320 K.; DH

Reaction thermochemistry 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 compiled as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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

C5H11O+ + 3-Pentanone = (C5H11O+ bullet 3-Pentanone)

By formula: C5H11O+ + C5H10O = (C5H11O+ bullet C5H10O)

Bond type: Hydrogen bonds of the type OH-O between organics

Bond type: Hydrogen bonds between protonated and neutral organics

Quantity Value Units Method Reference Comment
Deltar131.kJ/molPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase; M
Deltar121.kJ/molPHPMSSzulejko and McMahon, 1991gas phase; M
Deltar126.kJ/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity Value Units Method Reference Comment
Deltar149.J/mol*KPHPMSMeot-Ner (Mautner), Sieck, et al., 1994gas phase; M
Deltar141.J/mol*KPHPMSSzulejko and McMahon, 1991gas phase; M
Deltar131.J/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity Value Units Method Reference Comment
Deltar87.4kJ/molICRLarson and McMahon, 1982gas phase; switching reaction((CH3)2OH+)(CH3)2O, Entropy change calculated or estimated; Grimsrud and Kebarle, 1973, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M

C3H9Sn+ + 3-Pentanone = (C3H9Sn+ bullet 3-Pentanone)

By formula: C3H9Sn+ + C5H10O = (C3H9Sn+ bullet C5H10O)

Quantity Value Units Method Reference Comment
Deltar165.kJ/molPHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar132.J/mol*KN/AStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
95.8525.PHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

CH6N+ + 3-Pentanone = (CH6N+ bullet 3-Pentanone)

By formula: CH6N+ + C5H10O = (CH6N+ bullet C5H10O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity Value Units Method Reference Comment
Deltar108.kJ/molPHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar110.J/mol*KN/AMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
49.4549.PHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M

Chlorine anion + 3-Pentanone = (Chlorine anion bullet 3-Pentanone)

By formula: Cl- + C5H10O = (Cl- bullet C5H10O)

Quantity Value Units Method Reference Comment
Deltar59.0 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar82.0J/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)(CH3)2CO, Entropy change calculated or estimated; Larson and McMahon, 1984, 2; M
Quantity Value Units Method Reference Comment
Deltar34. ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M

(CAS Reg. No. 117951-42-5 bullet 42949672953-Pentanone) + 3-Pentanone = CAS Reg. No. 117951-42-5

By formula: (CAS Reg. No. 117951-42-5 bullet 4294967295C5H10O) + C5H10O = CAS Reg. No. 117951-42-5

Quantity Value Units Method Reference Comment
Deltar175. ± 8.8kJ/molN/AHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Deltar173. ± 12.kJ/molTherBoand, Houriet, et al., 1983gas phase; value altered from reference due to change in acidity scale; B

C5H9O- + Hydrogen cation = 3-Pentanone

By formula: C5H9O- + H+ = C5H10O

Quantity Value Units Method Reference Comment
Deltar1542. ± 9.2kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Deltar1518. ± 9.6kJ/molD-EAZimmerman, Reed, et al., 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar1512. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

C3H10N+ + 3-Pentanone = (C3H10N+ bullet 3-Pentanone)

By formula: C3H10N+ + C5H10O = (C3H10N+ bullet C5H10O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity Value Units Method Reference Comment
Deltar81.6kJ/molPHPMSMeot-Ner (Mautner), 1983gas phase; M
Quantity Value Units Method Reference Comment
Deltar123.J/mol*KPHPMSMeot-Ner (Mautner), 1983gas phase; M

Nitric oxide anion + 3-Pentanone = (Nitric oxide anion bullet 3-Pentanone)

By formula: NO- + C5H10O = (NO- bullet C5H10O)

Quantity Value Units Method Reference Comment
Deltar179.kJ/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

Hydrogen + 3-Pentanone = 3-Pentanol

By formula: H2 + C5H10O = C5H12O

Quantity Value Units Method Reference Comment
Deltar-56.74kJ/molEqkBuckley and Herington, 1965gas phase; ALS

3-Pentanol = Hydrogen + 3-Pentanone

By formula: C5H12O = H2 + C5H10O

Quantity Value Units Method Reference Comment
Deltar56.74kJ/molEqkBuckley and Herington, 1965gas phase; ALS

References

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

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

Meot-Ner (Mautner), Sieck, et al., 1994
Meot-Ner (Mautner), M.; Sieck, L.W.; Liebman, J.F.; Scheiner, S.; Duan, X., The Ionic Hydrogen Bond. 5. Polydentate and Solvent-Bridged Structures. Complexing of the Proton and the Hydronium Ions by Polyethers, J. Am. Chem. Soc., 1994, 116, 17, 7848, https://doi.org/10.1021/ja00096a047 . [all data]

Szulejko and McMahon, 1991
Szulejko, J.E.; McMahon, T.B., A Pulsed Electron Beam, Variable Temperature, High Pressure Mass Spectrometric Reevaluation of the Proton Affinity Difference Between 2-Methylpropene and Ammonia, Int. J. Mass Spectrom. Ion Proc., 1991, 109, 279, https://doi.org/10.1016/0168-1176(91)85109-Y . [all data]

Larson and McMahon, 1982
Larson, J.W.; McMahon, T.B., Formation, Thermochemistry, and Relative Stabilities of Proton - Bound dimers of Oxygen n - Donor Bases from Ion Cyclotron Resonance Solvent - Exchange Equilibria Measurements, J. Am. Chem. Soc., 1982, 104, 23, 6255, https://doi.org/10.1021/ja00387a016 . [all data]

Grimsrud and Kebarle, 1973
Grimsrud, E.P.; Kebarle, P., Gas Phase Ion Equilibria Studies of the Solvation of the Hydrogen Ion by Methanol, Dimethyl Ether and Water. Effect of Hydrogen Bonding, J. Am. Chem. Soc., 1973, 95, 24, 7939, https://doi.org/10.1021/ja00805a002 . [all data]

Lias, Liebman, et al., 1984
Lias, S.G.; Liebman, J.F.; Levin, R.D., Evaluated gas phase basicities and proton affinities of molecules heats of formation of protonated molecules, J. Phys. Chem. Ref. Data, 1984, 13, 695. [all data]

Keesee and Castleman, 1986
Keesee, R.G.; Castleman, A.W., Jr., Thermochemical data on Ggs-phase ion-molecule association and clustering reactions, J. Phys. Chem. Ref. Data, 1986, 15, 1011. [all data]

Stone and Splinter, 1984
Stone, J.A.; Splinter, D.E., A high-pressure mass spectrometric study of the binding of (CH3)3Sn+ to lewis bases in the gas phase, Int. J. Mass Spectrom. Ion Processes, 1984, 59, 169. [all data]

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria, J. Am. Chem. Soc., 1984, 106, 517. [all data]

Larson and McMahon, 1984, 2
Larson, J.W.; McMahon, T.B., Gas phase negative ion chemistry of alkylchloroformates, Can. J. Chem., 1984, 62, 675. [all data]

Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G., The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols, Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W . [all data]

Boand, Houriet, et al., 1983
Boand, G.; Houriet, R.; Baumann, T., The gas phase acidity of aliphatic alcohols, J. Am. Chem. Soc., 1983, 105, 2203. [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]

Meot-Ner (Mautner), 1983
Meot-Ner (Mautner), M., The Ionic Hydrogen Bond. 3. Multiple and -CH+...O- Bonds. Complexes of Ammonium Ions with Polyethers and Crown Ethers, J. Am. Chem. Soc., 1983, 105, 15, 4912, https://doi.org/10.1021/ja00353a012 . [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]


Notes

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