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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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 |
---|---|---|---|---|---|
ΔfH°gas | -58.08 | kcal/mol | N/A | Wiberg, Wasserman, et al., 1985 | Value computed using ΔfHliquid° value of -300.4±1.0 kj/mol from Wiberg, Wasserman, et al., 1985 and ΔvapH° value of 57.4 kj/mol from Sellers and Sunner, 1962.; DRB |
ΔfH°gas | -57.98 ± 0.40 | kcal/mol | Ccb | Sellers and Sunner, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = -57.63 kcal/mol; ALS |
ΔfH°gas | -58.05 | kcal/mol | N/A | Parks, Mosley, et al., 1950 | Value computed using ΔfHliquid° value of -300.3±0.2 kj/mol from Parks, Mosley, et al., 1950 and ΔvapH° value of 57.4 kj/mol from Sellers and Sunner, 1962.; DRB |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
25.198 | 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 |
25.356 | 300. | ||
33.941 | 400. | ||
41.592 | 500. | ||
47.971 | 600. | ||
53.239 | 700. | ||
57.670 | 800. | ||
61.424 | 900. | ||
64.625 | 1000. |
Gas phase ion energetics data
Go To: Top, Gas phase 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 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 (kcal/mol) | Reference | Comment |
---|---|---|
191. ± 1. | 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- + =
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 |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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]
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
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas ΔfH°gas Enthalpy of formation of gas 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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