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Cyclopentanol

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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:
DRB - Donald R. Burgess, Jr.
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-243.0kJ/molN/AWiberg, Wasserman, et al., 1985Value computed using «DELTA»fHliquid° value of -300.4±1.0 kj/mol from Wiberg, Wasserman, et al., 1985 and «DELTA»vapH° value of 57.4 kj/mol from Sellers and Sunner, 1962.; DRB
Deltafgas-242.6 ± 1.7kJ/molCcbSellers and Sunner, 1962Reanalyzed by Cox and Pilcher, 1970, Original value = -241.1 kJ/mol; ALS
Deltafgas-242.9kJ/molN/AParks, Mosley, et al., 1950Value computed using «DELTA»fHliquid° value of -300.3±0.2 kj/mol from Parks, Mosley, et al., 1950 and «DELTA»vapH° value of 57.4 kj/mol from Sellers and Sunner, 1962.; DRB

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
105.43298.15Kabo G.J., 1995Selected thermodynamic functions were calculated so that statistical entropy value at 340 K was put into agreement with the experimental one by adjusting the pseudorotational moment of inertia. Statistically calculated S(T) and Cp(T) values given in [ Thermodynamics Research Center, 1997] are 2-13 and 7-9 J/mol*K, respectively, larger than those of [ Kabo G.J., 1995].; GT
106.09300.
142.01400.
174.02500.
200.71600.
222.75700.
241.29800.
257.00900.
270.391000.

Condensed 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid-300.4 ± 1.0kJ/molCacWiberg, Wasserman, et al., 1985Trifluoroacetolysis; ALS
Deltafliquid-300.0 ± 1.7kJ/molCcbSellers and Sunner, 1962Reanalyzed by Cox and Pilcher, 1970, Original value = -298.6 kJ/mol; ALS
Deltafliquid-300.3 ± 0.2kJ/molCcbParks, Mosley, et al., 1950ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3096.7 ± 1.7kJ/molCcbSellers and Sunner, 1962Reanalyzed by Cox and Pilcher, 1970, Original value = -3098.1 ± 0.84 kJ/mol; Corresponding «DELTA»fliquid = -300.0 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-3096.5 ± 1.5kJ/molCcbParks, Mosley, et al., 1950Corresponding «DELTA»fliquid = -300.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid206.3J/mol*KN/AParks, Kennedy, et al., 1956Extrapolation below 80 K, 48.79 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
181.57298.15Benson and D'Arcy, 1986DH
185.4298.Conti, Gianni, et al., 1976DH
181.57298.15Conti, Gianni, et al., 1976DH
184.14298.15Parks, Kennedy, et al., 1956T = 80 to 300 K.; DH

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
Deltar1602. ± 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
Deltar1535. ± 4.6kJ/molN/AGarver, Yang, et al., 2011gas phase; B
Deltar1569. ± 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
Deltar-60.25 ± 0.67kJ/molCmWiberg, Crocker, et al., 1991liquid phase; ALS
Deltar-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
Deltar-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
Deltar54.9 ± 4.7kJ/molEqkFedoseenko, Yursha, et al., 1984gas phase; ALS
Deltar51.30kJ/molEqkCubberley and Mueller, 1946gas phase; ALS

Cyclohexanone + Cyclopentanol = Cyclohexanol + Cyclopentanone

By formula: C6H10O + C5H10O = C6H12O + C5H8O

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

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]

Sellers and Sunner, 1962
Sellers, P.; Sunner, S., Heats of combustion of cyclic ketones and alcohols, Acta Chem. Scand., 1962, 16, 46-52. [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]

Parks, Mosley, et al., 1950
Parks, G.S.; Mosley, J.R.; Peterson, P.V., Jr., Heats of combustion and formation of some organic compounds containing oxygen, J. Chem. Phys., 1950, 18, 152. [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]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Parks, Kennedy, et al., 1956
Parks, G.S.; Kennedy, W.D.; Gates, R.R.; Mosley, J.R.; Moore, G.E.; Renquist, M.L., Thermal data on organic compounds. XXVI. Some heat capacity, entropy and free energy data for seven compounds containing oxygen., Not In System, 1956, 78, 56-59. [all data]

Benson and D'Arcy, 1986
Benson, G.C.; D'Arcy, P.J., Excess isobaric heat capacities of some binary mixtures: (a C5-alkanol + n-heptane) at 298.15 K, J. Chem. Thermodynam., 1986, 18, 493-498. [all data]

Conti, Gianni, et al., 1976
Conti, G.; Gianni, P.; Matteoli, E.; Mengheri, M., Capacita termiche molari di alcuni composti organici mono- e bifunzionali nel liquido puro e in soluzione acquosa a 25C, Chim. Ind. (Milan), 1976, 58, 225. [all data]

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]

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

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