3-Pentanol
- Formula: C5H12O
- Molecular weight: 88.1482
- IUPAC Standard InChI: InChI=1S/C5H12O/c1-3-5(6)4-2/h5-6H,3-4H2,1-2H3
- IUPAC Standard InChIKey: AQIXEPGDORPWBJ-UHFFFAOYSA-N
- CAS Registry Number: 584-02-1
- 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: Diethyl carbinol; 3-Pentyl alcohol; (C2H5)2CHOH; Pentan-3-ol; sec-Amyl alcohol; Pentanol-3; UN 2706; Isoamyl alcohol; 1-Ethyl-1-propanol; NSC 8654; sec-Pentanol; sec-Pentyl alcohol
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics 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:
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 | -75.81 | kcal/mol | N/A | Sachek, Peshchenko, et al., 1974 | Value computed using ΔfHliquid° value of -368.9±0.8 kj/mol from Sachek, Peshchenko, et al., 1974 and ΔvapH° value of 51.7 kj/mol from Chao and Rossini, 1965.; DRB |
| ΔfH°gas | -75.21 ± 0.26 | kcal/mol | Eqk | Buckley and Herington, 1965 | Reanalyzed by Cox and Pilcher, 1970, Original value = -75.38 kcal/mol; ALS |
| ΔfH°gas | -76.14 ± 0.35 | kcal/mol | Ccb | Chao and Rossini, 1965 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°gas | 91.350 | cal/mol*K | N/A | Buckley E., 1965 | This value was obtained from the measurements of gas-phase equilibrium constants.; GT |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics 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:
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 | -88.17 ± 0.19 | kcal/mol | Ccb | Sachek, Peshchenko, et al., 1974 | Heat of combustion not reported; ALS |
| ΔfH°liquid | -88.51 ± 0.14 | kcal/mol | Ccb | Chao and Rossini, 1965 | see Rossini, 1934; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -791.65 ± 0.11 | kcal/mol | Ccb | Chao and Rossini, 1965 | see Rossini, 1934; Corresponding ΔfHºliquid = -88.50 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 57.29 | 298. | Conti, Gianni, et al., 1976 | DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, 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 evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
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
View reactions leading to C5H12O+ (ion structure unspecified)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 9.76 ± 0.02 | eV | N/A | N/A | L |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.78 ± 0.07 | EI | Bowen and Maccoll, 1984 | LBLHLM |
| 9.78 | EI | Holmes, Burgers, et al., 1982 | LBLHLM |
| 9.78 | EI | Holmes, Fingas, et al., 1981 | LLK |
| 9.73 | PE | Ashmore and Burgess, 1977 | LLK |
| 10.25 | PE | Ashmore and Burgess, 1977 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C3H6O+ | 9.84 ± 0.10 | C2H6 | EI | Bowen and Maccoll, 1984 | LBLHLM |
| C3H6O+ | 9.84 | C2H6 | EI | Holmes, Burgers, et al., 1982 | LBLHLM |
De-protonation reactions
C5H11O- + =
By formula: C5H11O- + H+ = C5H12O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 372.8 ± 2.0 | kcal/mol | CIDC | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
| ΔrH° | 372.7 ± 2.8 | kcal/mol | G+TS | Boand, Houriet, et al., 1983 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 366.2 ± 2.1 | kcal/mol | H-TS | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
| ΔrG° | 366.1 ± 2.7 | kcal/mol | CIDC | Boand, Houriet, et al., 1983 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Sachek, Peshchenko, et al., 1974
Sachek, A.I.; Peshchenko, A.D.; Andreevskii, D.N.,
Heats of formation of secondary pentanols and hexanols,
Russ. J. Phys. Chem. (Engl. Transl.), 1974, 48, 617. [all data]
Chao and Rossini, 1965
Chao, J.; Rossini, F.D.,
Heats of combustion, formation, and isomerization of nineteen alkanols,
J. Chem. Eng. Data, 1965, 10, 374-379. [all data]
Buckley and Herington, 1965
Buckley, E.; Herington, E.F.G.,
Equilibria in some secondary alcohol + hydrogen + ketone systems,
Trans. Faraday Soc., 1965, 61, 1618-1625. [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]
Buckley E., 1965
Buckley E.,
Equilibria in some secondary alcohol + hydrogen + ketone systems,
Trans. Faraday Soc., 1965, 61, 1618-1625. [all data]
Rossini, 1934
Rossini, F.D.,
Heats of combustion and of formation of the normal aliphatic alcohols in the gaseous and liquid states, and the energies of their atomic linkages,
J. Res. NBS, 1934, 13, 189-197. [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]
Bowen and Maccoll, 1984
Bowen, R.D.; Maccoll, A.,
Low energy, low temperature mass spectra,
Org. Mass Spectrom., 1984, 19, 379. [all data]
Holmes, Burgers, et al., 1982
Holmes, J.L.; Burgers, P.C.; Mollah, Y.A.,
Alkane elimination from ionized alkanols,
Org. Mass Spectrom., 1982, 17, 127. [all data]
Holmes, Fingas, et al., 1981
Holmes, J.L.; Fingas, M.; Lossing, F.P.,
Towards a general scheme for estimating the heats of formation of organic ions in the gas phase. Part I. Odd-electron cations,
Can. J. Chem., 1981, 59, 80. [all data]
Ashmore and Burgess, 1977
Ashmore, F.S.; Burgess, A.R.,
Study of Some Medium Size Alcohols and Hydroperoxides by Photoelectron Spectroscopy,
J. Chem. Soc. Faraday Trans. 2, 1977, 73, 1247. [all data]
Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G.,
The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols,
Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W
. [all data]
Boand, Houriet, et al., 1983
Boand, G.; Houriet, R.; Baumann, T.,
The gas phase acidity of aliphatic alcohols,
J. Am. Chem. Soc., 1983, 105, 2203. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°gas Entropy of gas at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas 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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