Cyclopentanol

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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 = Cyclopentanol

By formula: C5H9O- + H+ = C5H10O

Quantity Value Units Method Reference Comment
Δr1602. ± 19.kJ/molD-EAAlconcel and Continetti, 2002gas phase; derived acidity seems ca. 10 kcal/mol too weak, and EA likewise; B
Quantity Value Units Method Reference Comment
Δr1535. ± 4.6kJ/molN/AGarver, Yang, et al., 2011gas phase; B
Δr1569. ± 20.kJ/molH-TSAlconcel and Continetti, 2002gas phase; derived acidity seems ca. 10 kcal/mol too weak, and EA likewise; B

Cyclopentanone + Hydrogen = Cyclopentanol

By formula: C5H8O + H2 = C5H10O

Quantity Value Units Method Reference Comment
Δr-60.25 ± 0.67kJ/molCmWiberg, Crocker, et al., 1991liquid phase; ALS
Δr-51.25 ± 0.63kJ/molChydConn, Kistiakowsky, et al., 1939gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -52.3 ± 0.3 kJ/mol; At 355 K; ALS

Acetic acid, trifluoro-, anhydride + Cyclopentanol = Trifluoroacetic acid, cyclopentyl ester + Trifluoroacetic acid

By formula: C4F6O3 + C5H10O = C7H9F3O2 + C2HF3O2

Quantity Value Units Method Reference Comment
Δr-92.96 ± 0.23kJ/molCacWiberg, Wasserman, et al., 1985liquid phase; solvent: Trifluoroactic acid; Trifluoroacetolysis; ALS

Cyclopentanol = Cyclopentanone + Hydrogen

By formula: C5H10O = C5H8O + H2

Quantity Value Units Method Reference Comment
Δr54.9 ± 4.7kJ/molEqkFedoseenko, Yursha, et al., 1984gas phase; ALS
Δr51.30kJ/molEqkCubberley and Mueller, 1946gas phase; ALS

Cyclohexanone + Cyclopentanol = Cyclohexanol + Cyclopentanone

By formula: C6H10O + C5H10O = C6H12O + C5H8O

Quantity Value Units Method Reference Comment
Δr-11.6 ± 1.7kJ/molEqkFedoseenko, Yursha, et al., 1984gas phase; ALS

Mass spectrum (electron ionization)

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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-1501
NIST MS number 233847

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References

Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), Notes

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

Alconcel and Continetti, 2002
Alconcel, L.S.; Continetti, R.E., Dissociation dynamics and stability of cyclopentoxy and cyclopentoxide, Chem. Phys. Lett., 2002, 366, 5-6, 642-649, https://doi.org/10.1016/S0009-2614(02)01633-0 . [all data]

Garver, Yang, et al., 2011
Garver, J.M.; Yang, Z.B.; Kato, S.; Wren, S.W.; Vogelhuber, K.M.; Lineberger, W.C.; Bierbaum, V.M., Gas Phase Reactions of 1,3,5-Triazine: Proton Transfer, Hydride Transfer, and Anionic sigma-Adduct Formation, J. Am. Soc. Mass Spectrom., 2011, 22, 7, 1260-1272, https://doi.org/10.1007/s13361-011-0133-9 . [all data]

Wiberg, Crocker, et al., 1991
Wiberg, K.B.; Crocker, L.S.; Morgan, K.M., Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups, J. Am. Chem. Soc., 1991, 113, 3447-3450. [all data]

Conn, Kistiakowsky, et al., 1939
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VIII. Some further hydrogenations, including those of some acetylenes, J. Am. Chem. Soc., 1939, 61, 1868-1876. [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]

Wiberg, Wasserman, et al., 1985
Wiberg, K.B.; Wasserman, D.J.; Martin, E.J.; Murcko, M.A., Enthalpies of hydration of alkenes. 3. Cycloalkenes, J. Am. Chem. Soc., 1985, 107, 6019-6022. [all data]

Fedoseenko, Yursha, et al., 1984
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya., Equilibrium of cyclopentanol dehydrogenation and hydrogen disproportionation in the cyclopentanol-cyclohexanone system, Dokl. Akad. Nauk BSSR, 1984, 28, 1109-1112. [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]


Notes

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