Pentanoic acid

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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

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Individual Reactions

C5H9O2- + Hydrogen cation = Pentanoic acid

By formula: C5H9O2- + H+ = C5H10O2

Quantity Value Units Method Reference Comment
Δr346.2 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Δr346.1 ± 2.4kcal/molG+TSMcLuckey, Cameron, et al., 1981gas phase; B
Quantity Value Units Method Reference Comment
Δr339.2 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Δr339.1 ± 2.3kcal/molCIDCMcLuckey, Cameron, et al., 1981gas phase; B

2Hydrogen + 3-Pentynoic acid = Pentanoic acid

By formula: 2H2 + C5H6O2 = C5H10O2

Quantity Value Units Method Reference Comment
Δr-65.8 ± 1.2kcal/molChydFlitcroft and Skinner, 1958liquid phase; ALS

Gas phase ion energetics data

Go To: Top, 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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

Ionization energy determinations

IE (eV) Method Reference Comment
10.53PEWatanabe, Yokoyama, et al., 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H4O2+10.8 ± 0.1C3H6EIAudier, Milliet, et al., 1985LBLHLM
C2H5O2+10.4 ± 0.1C3H5EIAudier, Milliet, et al., 1985LBLHLM
C2H402+10.56 ± 0.05C3H6EIHolmes and Lossing, 1980LLK
C2H402+10.56C3H6EIHolmes and Lossing, 1980, 2LLK

De-protonation reactions

C5H9O2- + Hydrogen cation = Pentanoic acid

By formula: C5H9O2- + H+ = C5H10O2

Quantity Value Units Method Reference Comment
Δr346.2 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Δr346.1 ± 2.4kcal/molG+TSMcLuckey, Cameron, et al., 1981gas phase; B
Quantity Value Units Method Reference Comment
Δr339.2 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Δr339.1 ± 2.3kcal/molCIDCMcLuckey, Cameron, et al., 1981gas phase; B

References

Go To: Top, Reaction 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.

Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P., Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria, Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092 . [all data]

McLuckey, Cameron, et al., 1981
McLuckey, S.A.; Cameron, D.; Cooks, R.G., Proton affinities from the dissociation of proton bound dimers, J. Am. Chem. Soc., 1981, 103, 1313. [all data]

Flitcroft and Skinner, 1958
Flitcroft, T.L.; Skinner, H.A., Heats of hydrogenation Part 2.-Acetylene derivatives, Trans. Faraday Soc., 1958, 54, 47-53. [all data]

Watanabe, Yokoyama, et al., 1973
Watanabe, I.; Yokoyama, Y.; Ikeda, S., Lone pair ionization potentials of carboxylic acids determined by He(I) photoelectron spectroscopy, Bull. Chem. Soc. Jpn., 1973, 46, 1959. [all data]

Audier, Milliet, et al., 1985
Audier, H.; Milliet, A.; Sozzi, G., Isomerisation des cation radicaux acides pentanoique et methyl-3-butanoique in phase gazeuse, Bull. Soc. Chim. France, 1985, 5, 833. [all data]

Holmes and Lossing, 1980
Holmes, J.L.; Lossing, F.P., Thermochemistry and unimolecular reactions of ionized acetic acid and its enol in the gas phase., J. Am. Chem. Soc., 1980, 102, 3732. [all data]

Holmes and Lossing, 1980, 2
Holmes, J.L.; Lossing, F.P., Gas-phase heats of formation of keto and enol ions of carbonyl compounds., J. Am. Chem. Soc., 1980, 102, 1591. [all data]


Notes

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