Cyclopentanol

Formula: C₅H₁₀O
Molecular weight: 86.1323
IUPAC Standard InChI: InChI=1S/C5H10O/c6-5-3-1-2-4-5/h5-6H,1-4H2
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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Gas phase thermochemistry data

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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
Δ_fH°_gas	-243.0	kJ/mol	N/A	Wiberg, Wasserman, et al., 1985	Value computed using Δ_fH_liquid° value of -300.4±1.0 kj/mol from Wiberg, Wasserman, et al., 1985 and Δ_vapH° value of 57.4 kj/mol from Sellers and Sunner, 1962.; DRB
Δ_fH°_gas	-242.6 ± 1.7	kJ/mol	Ccb	Sellers and Sunner, 1962	Reanalyzed by Cox and Pilcher, 1970, Original value = -241.1 kJ/mol; ALS
Δ_fH°_gas	-242.9	kJ/mol	N/A	Parks, Mosley, et al., 1950	Value computed using Δ_fH_liquid° value of -300.3±0.2 kj/mol from Parks, Mosley, et al., 1950 and Δ_vapH° value of 57.4 kj/mol from Sellers and Sunner, 1962.; DRB

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
105.43	298.15	Kabo G.J., 1995	Selected 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
106.09	300.
142.01	400.
174.02	500.
200.71	600.
222.75	700.
241.29	800.
257.00	900.
270.39	1000.

Gas phase ion energetics data

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Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₅H₁₀O⁺ (ion structure unspecified)

Proton affinity at 298K

Proton affinity (kJ/mol)	Reference	Comment
798. ± 6.	Cao and Holmes, 2001	MM

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.72	PI	Traeger, 1985	LBLHLM
9.58 ± 0.06	EI	Holmes, Yuan, et al., 1977	LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₃H₅O⁺	9.72	C₂H₅	PI	Traeger, 1985	LBLHLM
C₃H₆O⁺	9.98	C₂H₄	EI	Holmes and Lossing, 1980	LLK
C₅H₈⁺	9.66 ± 0.06	H₂O	EI	Holmes, Yuan, et al., 1977	LLK
C₅H₈⁺	9.49	H₂O	EI	Lewis and Hamill, 1970	RDSH
H₂O⁺	13.23	C₅H₈	EI	Lewis and Hamill, 1970	RDSH

De-protonation reactions

C₅H₉O^- + = Cyclopentanol

By formula: C₅H₉O^- + H⁺ = C₅H₁₀O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1602. ± 19.	kJ/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
Δ_rG°	1535. ± 4.6	kJ/mol	N/A	Garver, Yang, et al., 2011	gas phase; B
Δ_rG°	1569. ± 20.	kJ/mol	H-TS	Alconcel and Continetti, 2002	gas phase; derived acidity seems ca. 10 kcal/mol too weak, and EA likewise; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

SOLUTION (10% CCl4 FOR 3800-1340, 10% CS2 FOR 1340-450 CM^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

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

gas; HP-GC/MS/IRD

References

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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]

Cao and Holmes, 2001
Cao, J.; Holmes, J.L., Determination of the proton affinities of secondary alcohols from the dissocation of proton-bound molecular trios, European J. Mass Spectrom., 2001, 7, 243-247. [all data]

Traeger, 1985
Traeger, J.C., Heat of formation for the propanoyl cation by photoionization mass spectrometry, Org. Mass Spectrom., 1985, 20, 223. [all data]

Holmes, Yuan, et al., 1977
Holmes, J.L.; Yuan, D.; Rye, R.T.B., Metastable ion studies VII-Loss of water from the molecular ion of cyclopentanol, Org. Mass Spectrom., 1977, 12, 254. [all data]

Holmes and Lossing, 1980
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]

Lewis and Hamill, 1970
Lewis, D.; Hamill, W.H., Excited states of neutral molecular fragments from appearance potentials by electron impact in a mass spectrometer, J. Chem. Phys., 1970, 52, 6348. [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]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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