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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

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil413. ± 2.KAVGN/AAverage of 10 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus254.15KN/ATimmermans, 1952Uncertainty assigned by TRC = 1. K; TRC
Tfus253.KN/AWhite and Bishop, 1940Crystal phase 1 phase; Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Ttriple255.6KN/AKabo, Diky, et al., 1995Crystal phase 1 phase; Uncertainty assigned by TRC = 0.3 K; TRC
Ttriple256.0KN/AWuerflinger and Kreutzenbeck, 1978Crystal phase 1 phase; Uncertainty assigned by TRC = 0.5 K; TRC
Ttriple257.4KN/AParks, Kennedy, et al., 1956, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; see 1978 wuekre 0 for phase identification; TRC
Quantity Value Units Method Reference Comment
Tc620. ± 1.KN/AGude and Teja, 1995 
Tc619.5KN/AAmbrose and Ghiassee, 1987Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Pc49. ± 1.barN/AGude and Teja, 1995 
Pc49.00barN/AAmbrose and Ghiassee, 1987Uncertainty assigned by TRC = 1.00 bar; TRC
Quantity Value Units Method Reference Comment
Deltavap57. ± 1.kJ/molAVGN/AAverage of 8 values; Individual data points

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
52.7361.A,EBAmbrose and Ghiassee, 1987, 2Based on data from 346. - 437. K.; AC
57.1294.N/ACabani, Conti, et al., 1975Based on data from 279. - 314. K.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
1.54257.4Domalski and Hearing, 1996AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
18.28202.8Domalski and Hearing, 1996CAL
5.98257.4

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
3.707202.8crystaline, IIcrystaline, IParks, Kennedy, et al., 1956DH
1.536257.4crystaline, IliquidParks, Kennedy, et al., 1956DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
18.28202.8crystaline, IIcrystaline, IParks, Kennedy, et al., 1956DH
5.97257.4crystaline, IliquidParks, Kennedy, et al., 1956DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), 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- + 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

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes

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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Additional Data

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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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.

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]

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]

White and Bishop, 1940
White, A.H.; Bishop, W.S., Dielectric Evidence of Molecular Rotation in the Crystals of Certain Non-aromatic Compounds, J. Am. Chem. Soc., 1940, 62, 8-16. [all data]

Kabo, Diky, et al., 1995
Kabo, G.Ya.; Diky, V.V.; Kozyro, A.A.; Krasulin, A.P.; Sevruk, V.M., Thermodynamic properties, conformational composition, and phase transitions of cyclopentanol, J. Chem. Thermodyn., 1995, 27, 953-67. [all data]

Wuerflinger and Kreutzenbeck, 1978
Wuerflinger, A.; Kreutzenbeck, J., J. Phys. Chem. Solids, 1978, 39, 193. [all data]

Parks, Kennedy, et al., 1956, 2
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, J. Am. Chem. Soc., 1956, 78, 56-9. [all data]

Gude and Teja, 1995
Gude, M.; Teja, A.S., Vapor-Liquid Critical Properties of Elements and Compounds. 4. Aliphatic Alkanols, J. Chem. Eng. Data, 1995, 40, 1025-1036. [all data]

Ambrose and Ghiassee, 1987
Ambrose, D.; Ghiassee, N.B., Vapor Pressures and Critical Temperatures and Critical Pressures of C5 and C6 Cyclic Alcohols and Ketones, J. Chem. Thermodyn., 1987, 19, 903. [all data]

Ambrose and Ghiassee, 1987, 2
Ambrose, D.; Ghiassee, N.B., Vapour pressures and critical temperatures and critical pressures of C5 and C6 cyclic alcohols and ketones, The Journal of Chemical Thermodynamics, 1987, 19, 9, 903-909, https://doi.org/10.1016/0021-9614(87)90036-X . [all data]

Cabani, Conti, et al., 1975
Cabani, Sergio; Conti, G.; Mollica, V.; Lepori, L., Thermodynamic study of dilute aqueous solutions of organic compounds. Part 4.---Cyclic and straight chain secondary alcohols, J. Chem. Soc., Faraday Trans. 1, 1975, 71, 0, 1943, https://doi.org/10.1039/f19757101943 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References