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2-Butanone

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Reaction 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:
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
RCD - Robert C. Dunbar

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

C4H9O+ + 2-Butanone = (C4H9O+ bullet 2-Butanone)

By formula: C4H9O+ + C4H8O = (C4H9O+ bullet C4H8O)

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

Quantity Value Units Method Reference Comment
Deltar127.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
Deltar129.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
Deltar88.7kJ/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

C5H11O+ + 2-Butanone = (C5H11O+ bullet 2-Butanone)

By formula: C5H11O+ + C4H8O = (C5H11O+ bullet C4H8O)

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

Quantity Value Units Method Reference Comment
Deltar123.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
Deltar123.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
Deltar86.6kJ/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

C4H7O- + Hydrogen cation = 2-Butanone

By formula: C4H7O- + H+ = C4H8O

Quantity Value Units Method Reference Comment
Deltar1536. ± 12.kJ/molG+TSChyall, Brickhouse, et al., 1994gas phase; Primary and secondary sites are of equal acidity by equilibration. Acidity from Zimmerman, Reed, et al., 1977; B
Deltar1545. ± 10.kJ/molD-EAZimmerman, Reed, et al., 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar1508. ± 11.kJ/molIMREChyall, Brickhouse, et al., 1994gas phase; Primary and secondary sites are of equal acidity by equilibration. Acidity from Zimmerman, Reed, et al., 1977; B
Deltar1516. ± 11.kJ/molH-TSZimmerman, Reed, et al., 1977gas phase; B

C3H9Sn+ + 2-Butanone = (C3H9Sn+ bullet 2-Butanone)

By formula: C3H9Sn+ + C4H8O = (C3H9Sn+ bullet C4H8O)

Quantity Value Units Method Reference Comment
Deltar164.kJ/molPHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar137.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
92.5525.PHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

CH6N+ + 2-Butanone = (CH6N+ bullet 2-Butanone)

By formula: CH6N+ + C4H8O = (CH6N+ bullet C4H8O)

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

Quantity Value Units Method Reference Comment
Deltar105.kJ/molPHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar100.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
47.7553.PHPMSMeot-Ner, 1984gas phase; Entropy change calculated or estimated; M

Chlorine anion + 2-Butanone = (Chlorine anion bullet 2-Butanone)

By formula: Cl- + C4H8O = (Cl- bullet C4H8O)

Quantity Value Units Method Reference Comment
Deltar61.9 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar87.9J/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
Deltar36. ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M

Hydrogen + 2-Butanone = 2-Butanol

By formula: H2 + C4H8O = C4H10O

Quantity Value Units Method Reference Comment
Deltar-54.18kJ/molEqkBuckley and Herington, 1965gas phase; ALS
Deltar-54.3 ± 0.4kJ/molChydDolliver, Gresham, et al., 1938gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -55.2 ± 0.4 kJ/mol; At 355 °K; ALS

C4H7O- + Hydrogen cation = 2-Butanone

By formula: C4H7O- + H+ = C4H8O

Quantity Value Units Method Reference Comment
Deltar1678. ± 17.kJ/molCIDTGraul and Squires, 1990gas phase; B
Deltar<1711.3kJ/molCIDTGraul and Squires, 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar1646. ± 17.kJ/molH-TSGraul and Squires, 1990gas phase; B

Nitric oxide anion + 2-Butanone = (Nitric oxide anion bullet 2-Butanone)

By formula: NO- + C4H8O = (NO- bullet C4H8O)

Quantity Value Units Method Reference Comment
Deltar177.kJ/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

C4H7O- + Hydrogen cation = 2-Butanone

By formula: C4H7O- + H+ = C4H8O

Quantity Value Units Method Reference Comment
Deltar1540. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Deltar1512. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

(CAS Reg. No. 35730-33-7 bullet 42949672952-Butanone) + 2-Butanone = CAS Reg. No. 35730-33-7

By formula: (CAS Reg. No. 35730-33-7 bullet 4294967295C4H8O) + C4H8O = CAS Reg. No. 35730-33-7

Quantity Value Units Method Reference Comment
Deltar164. ± 9.2kJ/molN/ATaft, 1987gas phase; value altered from reference due to change in acidity scale; B

2-Butanol = Hydrogen + 2-Butanone

By formula: C4H10O = H2 + C4H8O

Quantity Value Units Method Reference Comment
Deltar54.22kJ/molEqkCubberley and Mueller, 1946gas phase; ALS
Deltar57.170kJ/molEqkKolb and Burwell, 1945gas phase; ALS

Magnesium ion (1+) + 2-Butanone = (Magnesium ion (1+) bullet 2-Butanone)

By formula: Mg+ + C4H8O = (Mg+ bullet C4H8O)

Quantity Value Units Method Reference Comment
Deltar280.kJ/molICROperti, Tews, et al., 1988gas phase; switching reaction,Thermochemical ladder(CH3OH); M

2,2-Dimethoxybutane + Water = 2Methyl Alcohol + 2-Butanone

By formula: C6H14O2 + H2O = 2CH4O + C4H8O

Quantity Value Units Method Reference Comment
Deltar19.33 ± 0.04kJ/molCmWiberg and Squires, 1979liquid phase; Heat of hydrolysis; ALS

Hydrogen iodide + 3-Iodo-2-butanone = Iodine + 2-Butanone

By formula: HI + C4H7IO = I2 + C4H8O

Quantity Value Units Method Reference Comment
Deltar-42.7kJ/molKinSolly, Golden, et al., 1970gas phase; ALS

Hydrogen + Methyl vinyl ketone = 2-Butanone

By formula: H2 + C4H6O = C4H8O

Quantity Value Units Method Reference Comment
Deltar-550.6kJ/molChydVeselova and Sul'man, 1980liquid phase; ALS

Sodium ion (1+) + 2-Butanone = (Sodium ion (1+) bullet 2-Butanone)

By formula: Na+ + C4H8O = (Na+ bullet C4H8O)

Quantity Value Units Method Reference Comment
Deltar131. ± 7.1kJ/molCIDTMoision and Armentrout, 2002RCD

References

Go To: Top, Reaction thermochemistry data, Notes

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

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]

Chyall, Brickhouse, et al., 1994
Chyall, L.J.; Brickhouse, M.D.; Schnute, M.E.; Squires, R.R., Kinetic versus thermodynamic control in the deprotonation of unsymmetrical ketones in the gas phase, J. Am. Chem. Soc., 1994, 116, 19, 8681, https://doi.org/10.1021/ja00098a031 . [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]

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]

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]

Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E., Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds, J. Am. Chem. Soc., 1938, 60, 440-450. [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]

Graul and Squires, 1990
Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [all data]

Graul and Squires, 1988
Graul, S.T.; Squires, R.R., On the Existence of Alkyl Carbanions in the Gas Phase, J. Am. Chem. Soc., 1988, 110, 2, 607, https://doi.org/10.1021/ja00210a054 . [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]

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]

Taft, 1987
Taft, R.W., The Nature and Analysis of Substitutent Electronic Effects, Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Cubberley and Mueller, 1946
Cubberley, A.H.; Mueller, M.B., Equilibrium studies on the dehydrogenation of primary and secondary alcohols. I. 2-Butanol, 2-octanol, cyclopentanol and benzyl alcohol, J. Am. Chem. Soc., 1946, 68, 1149-1151. [all data]

Kolb and Burwell, 1945
Kolb, H.J.; Burwell, R.L., Jr., Equilibrium in the dehydrogenation of secondary propyl and butyl alcohols, J. Am. Chem. Soc., 1945, 67, 1084-1088. [all data]

Operti, Tews, et al., 1988
Operti, L.; Tews, E.C.; Freiser, B.S., Determination of Gas-Phase Ligand Binding Energies to Mg+ by FTMS Techniques, J. Am. Chem. Soc., 1988, 110, 12, 3847, https://doi.org/10.1021/ja00220a020 . [all data]

Wiberg and Squires, 1979
Wiberg, K.B.; Squires, R.R., Thermodynamics of hydrolysis aliphatic ketals. An entropy component of steric effects, J. Am. Chem. Soc., 1979, 101, 5512-5515. [all data]

Solly, Golden, et al., 1970
Solly, R.K.; Golden, D.M.; Benson, S.W., Kinetics and thermochemistry of the gas phase reaction of methyl ethyl ketone with iodine. II. The heat of formation and unimolecular decomposition of 2-iodo-3-butanone, Int. J. Chem. Kinet., 1970, 2, 393-407. [all data]

Veselova and Sul'man, 1980
Veselova, M.E.; Sul'man, E.M., Effect of the chemical structure of «alpha»,«beta»-unsaturated esters and ketones on the selectivity of their hydrogenation, Svoistva Veshchestv i Stroenie Molekul, Kalinin, 1980, 140-143. [all data]

Moision and Armentrout, 2002
Moision, R.M.; Armentrout, P.B., Experimental and Theoretical Dissection of Sodium Cation/Glycine Interactions, J. Phys. Chem A, 2002, 106, 43, 10350, https://doi.org/10.1021/jp0216373 . [all data]


Notes

Go To: Top, Reaction thermochemistry data, References