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2-Butanone, 3-methyl-

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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:
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

C5H9O- + Hydrogen cation = 2-Butanone, 3-methyl-

By formula: C5H9O- + H+ = C5H10O

Quantity Value Units Method Reference Comment
Deltar1545. ± 11.kJ/molG+TSChyall, Brickhouse, et al., 1994gas phase; By equilibration, more substituted site is less acidic than Me by 2.3 kcal/mol; B
Quantity Value Units Method Reference Comment
Deltar1518. ± 10.kJ/molIMREChyall, Brickhouse, et al., 1994gas phase; By equilibration, more substituted site is less acidic than Me by 2.3 kcal/mol; B

C5H9O- + Hydrogen cation = 2-Butanone, 3-methyl-

By formula: C5H9O- + H+ = C5H10O

Quantity Value Units Method Reference Comment
Deltar1537. ± 9.2kJ/molG+TSCumming and Kebarle, 1978gas phase; Structure assignment revised to less-substituted site: Chyall, Brickhouse, et al., 1994; B
Quantity Value Units Method Reference Comment
Deltar1508. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; Structure assignment revised to less-substituted site: Chyall, Brickhouse, et al., 1994; B

(CAS Reg. No. 60375-60-2 bullet 42949672952-Butanone, 3-methyl-) + 2-Butanone, 3-methyl- = CAS Reg. No. 60375-60-2

By formula: (CAS Reg. No. 60375-60-2 bullet 4294967295C5H10O) + C5H10O = CAS Reg. No. 60375-60-2

Quantity Value Units Method Reference Comment
Deltar169. ± 8.8kJ/molN/AHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.; B
Deltar168. ± 12.kJ/molTherBoand, Houriet, et al., 1983gas phase; value altered from reference due to change in acidity scale; B

2,2-Dimethoxy-3-methylbutane + Water = 2-Butanone, 3-methyl- + 2Methyl Alcohol

By formula: C7H16O2 + H2O = C5H10O + 2CH4O

Quantity Value Units Method Reference Comment
Deltar20.33 ± 0.04kJ/molCmWiberg and Squires, 1979liquid phase; Heat of hydrolysis; ALS

2-Butanol, 3-methyl- = Hydrogen + 2-Butanone, 3-methyl-

By formula: C5H12O = H2 + C5H10O

Quantity Value Units Method Reference Comment
Deltar53.8 ± 1.6kJ/molEqkConnett, 1970gas phase; ALS

References

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

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]

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]

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]

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]

Connett, 1970
Connett, J.E., Chemical equilibria. Part III. Dehydrogenation of pentan-1-ol, pentan-2-ol, and 3-methylbutan-2-ol, J. Chem. Soc. A, 1970, 1284-1286. [all data]


Notes

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