Cyclopentanol
- Formula: C5H10O
- Molecular weight: 86.1323
- IUPAC Standard InChIKey: XCIXKGXIYUWCLL-UHFFFAOYSA-N
- CAS Registry Number: 96-41-3
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Cyclopentyl alcohol; Hydroxycyclopentane; UN 2244
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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 |
---|---|---|---|---|---|
ΔfH°liquid | -71.80 ± 0.25 | kcal/mol | Cac | Wiberg, Wasserman, et al., 1985 | Trifluoroacetolysis; ALS |
ΔfH°liquid | -71.71 ± 0.41 | kcal/mol | Ccb | Sellers and Sunner, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = -71.37 kcal/mol; ALS |
ΔfH°liquid | -71.77 ± 0.04 | kcal/mol | Ccb | Parks, Mosley, et al., 1950 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -740.12 ± 0.40 | kcal/mol | Ccb | Sellers and Sunner, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = -740.47 ± 0.20 kcal/mol; Corresponding ΔfHºliquid = -71.71 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -740.07 ± 0.37 | kcal/mol | Ccb | Parks, Mosley, et al., 1950 | Corresponding ΔfHºliquid = -71.76 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 49.31 | cal/mol*K | N/A | Parks, Kennedy, et al., 1956 | Extrapolation below 80 K, 48.79 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
43.396 | 298.15 | Benson and D'Arcy, 1986 | DH |
44.31 | 298. | Conti, Gianni, et al., 1976 | DH |
43.396 | 298.15 | Conti, Gianni, et al., 1976 | DH |
44.011 | 298.15 | Parks, Kennedy, et al., 1956 | T = 80 to 300 K.; DH |
Reaction thermochemistry data
Go To: Top, Condensed phase 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
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- + =
By formula: C5H9O- + H+ = C5H10O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 383.0 ± 4.6 | kcal/mol | D-EA | Alconcel and Continetti, 2002 | gas phase; derived acidity seems ca. 10 kcal/mol too weak, and EA likewise; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 366.9 ± 1.1 | kcal/mol | N/A | Garver, Yang, et al., 2011 | gas phase; B |
ΔrG° | 374.9 ± 4.7 | kcal/mol | H-TS | Alconcel and Continetti, 2002 | gas phase; derived acidity seems ca. 10 kcal/mol too weak, and EA likewise; B |
By formula: C5H8O + H2 = C5H10O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -14.40 ± 0.16 | kcal/mol | Cm | Wiberg, Crocker, et al., 1991 | liquid phase; ALS |
ΔrH° | -12.25 ± 0.15 | kcal/mol | Chyd | Conn, Kistiakowsky, et al., 1939 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -12.50 ± 0.06 kcal/mol; At 355 K; ALS |
By formula: C4F6O3 + C5H10O = C7H9F3O2 + C2HF3O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -22.219 ± 0.056 | kcal/mol | Cac | Wiberg, Wasserman, et al., 1985 | liquid phase; solvent: Trifluoroactic acid; Trifluoroacetolysis; ALS |
By formula: C5H10O = C5H8O + H2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 13.1 ± 1.1 | kcal/mol | Eqk | Fedoseenko, Yursha, et al., 1984 | gas phase; ALS |
ΔrH° | 12.26 | kcal/mol | Eqk | Cubberley and Mueller, 1946 | gas phase; ALS |
By formula: C6H10O + C5H10O = C6H12O + C5H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -2.77 ± 0.41 | kcal/mol | Eqk | Fedoseenko, Yursha, et al., 1984 | gas phase; ALS |
References
Go To: Top, 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]
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, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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