2H-Pyran-2-one, tetrahydro-
- Formula: C5H8O2
- Molecular weight: 100.1158
- IUPAC Standard InChIKey: OZJPLYNZGCXSJM-UHFFFAOYSA-N
- CAS Registry Number: 542-28-9
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: δ-Valerolactone; δ-Valeryllactone; Pentanoic acid, 5-hydroxy-, δ-lactone; Tetrahydro-2-pyranone; 5-Valerolactone; Valeric acid, δ-hydroxy-, δ-lactone; 5-Hydroxypentanoic acid δ-lactone; 1-Oxacyclohexan-2-one; Tetrahydro-2H-pyran-2-one; Delta-valerolactone; δ-Pentalactone; 5-Pentanolide; Cyclopentanolide; Tetrahydropyran-2-one; NSC 6247; Pentan-5-olide; γ-Valerolactone
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Condensed phase thermochemistry data
Go To: Top, Phase change data, 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:
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 | -436. ± 3. | kJ/mol | Cm | Wiberg and Waldron, 1991 | Heat of reduction; ALS |
ΔfH°liquid | -437.6 ± 0.8 | kJ/mol | Ccb | Leitao, Pilcher, et al., 1990 | See Brown, Conn, et al., 1989; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2673.3 ± 0.5 | kJ/mol | Ccb | Leitao, Pilcher, et al., 1990 | See Brown, Conn, et al., 1989; Corresponding ΔfHºliquid = -437.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 219.0 | J/mol*K | N/A | Lebedev and Yevstropov, 1983 | DH |
S°liquid | 219.0 | J/mol*K | N/A | Yevstropov, Lebedev, et al., 1982 | DH |
S°liquid | 219.0 | J/mol*K | N/A | Evstopov, Lebedev, et al., 1981 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
171.6 | 298.15 | Lebedev and Yevstropov, 1983 | T = 13.8 to 340 K.; DH |
171.6 | 298.15 | Yevstropov, Lebedev, et al., 1982 | T = 5 to 340 K.; DH |
171.6 | 298.15 | Evstopov, Lebedev, et al., 1981 | T = 5 to 340 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, 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:
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.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 492.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 262.8 | K | N/A | Anonymous, 1955 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 262.82 | K | N/A | Lebedev and Yevstropov, 1983, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 262.82 | K | N/A | Evstropov, Lebedev, et al., 1982 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 262.82 | K | N/A | Evstopov, Lebedev, et al., 1981 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; C3 to C2: Non-isothermal transition; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 59. ± 2. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
332.2 | 0.0007 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
52.4 ± 0.2 | 410. | EB | Wiberg and Waldron, 1991 | Based on data from 393. to 428. K.; AC |
48.6 | 387. | N/A | Schuette and Thomas, 1930 | Based on data from 342. to 433. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.53 | 263. | Acree, 1991 | AC |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.457 | 118.1 | crystaline, IV | crystaline, III | Lebedev and Yevstropov, 1983 | DH |
0.310 | 122. to 155. | crystaline, III | crystaline, II | Lebedev and Yevstropov, 1983 | DH |
0.205 | 180. to 225. | crystaline, II | crystaline, I | Lebedev and Yevstropov, 1983 | DH |
10.530 | 262.82 | crystaline, I | liquid | Lebedev and Yevstropov, 1983 | DH |
0.457 | 118. | crystaline, IV | crystaline, III | Yevstropov, Lebedev, et al., 1982 | DH |
0.310 | 122. to 155. | crystaline, III | crystaline, II | Yevstropov, Lebedev, et al., 1982 | DH |
0.205 | 180. to 225. | crystaline, II | crystaline, I | Yevstropov, Lebedev, et al., 1982 | DH |
10.530 | 262.82 | crystaline, I | liquid | Yevstropov, Lebedev, et al., 1982 | DH |
0.457 | 118.1 | crystaline, IV | crystaline, III | Evstopov, Lebedev, et al., 1981 | DH |
0.310 | 122. to 155. | crystaline, III | crystaline, II | Evstopov, Lebedev, et al., 1981 | DH |
0.205 | 180. to 225. | crystaline, II | crystaline, I | Evstopov, Lebedev, et al., 1981 | DH |
10.530 | 262.82 | crystaline, I | liquid | Evstopov, Lebedev, et al., 1981 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
3.88 | 118.1 | crystaline, IV | crystaline, III | Lebedev and Yevstropov, 1983 | DH |
2.2 | 122. to 155. | crystaline, III | crystaline, II | Lebedev and Yevstropov, 1983 | DH |
0.90 | 180. to 225. | crystaline, II | crystaline, I | Lebedev and Yevstropov, 1983 | DH |
39.46 | 262.82 | crystaline, I | liquid | Lebedev and Yevstropov, 1983 | DH |
3.88 | 118. | crystaline, IV | crystaline, III | Yevstropov, Lebedev, et al., 1982 | DH |
2.2 | 122. to 155. | crystaline, III | crystaline, II | Yevstropov, Lebedev, et al., 1982 | DH |
0.90 | 180. to 225. | crystaline, II | crystaline, I | Yevstropov, Lebedev, et al., 1982 | DH |
39.46 | 262.82 | crystaline, I | liquid | Yevstropov, Lebedev, et al., 1982 | DH |
3.88 | 118.1 | crystaline, IV | crystaline, III | Evstopov, Lebedev, et al., 1981 | DH |
2.2 | 122. to 155. | crystaline, III | crystaline, II | Evstopov, Lebedev, et al., 1981 | DH |
0.90 | 180. to 225. | crystaline, II | crystaline, I | Evstopov, Lebedev, et al., 1981 | DH |
39.46 | 262.82 | crystaline, I | liquid | Evstopov, Lebedev, et al., 1981 | DH |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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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 | Chemical Concepts |
NIST MS number | 151343 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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 and Waldron, 1991
Wiberg, K.B.; Waldron, R.F.,
Lactones. 2. Enthalpies of hydrolysis, reduction, and formation of the C4-C13 monocyclic lactones. strain energies and conformations,
J. Am. Chem. Soc., 1991, 113, 7697-7705. [all data]
Leitao, Pilcher, et al., 1990
Leitao, M.L.P.; Pilcher, H.; Meng-Yan, Y.; Brown, J.M.; Conn, A.D.,
Enthalpies of combustion of γ-butyrolactone, γ-valerolactone, and δ-valerolactone,
J. Chem. Thermodyn., 1990, 22, 885-891. [all data]
Brown, Conn, et al., 1989
Brown, J.M.; Conn, A.D.; Pilcher, G.; Leitao, M.L.P.; Yang, M.-Y.,
On the strain energy of 5-ring and 6-ring lactones,
J. Chem. Soc., Chem. Commun., 1989, 1817-1819. [all data]
Lebedev and Yevstropov, 1983
Lebedev, B.V.; Yevstropov, A.A.,
Thermodynamics of β-propiolactone, t-butyrolactone, d-valerolactone, and e-caprolactone from 13.8 to 340 K,
J. Chem. Thermodynam., 1983, 15, 115-128. [all data]
Yevstropov, Lebedev, et al., 1982
Yevstropov, A.A.; Lebedev, B.V.; Kulagina, T.G.; Lebedev, N.K.,
Calorimetric study of d-valerolactone, poly-d-valerolactone and of the process of polymerization of d-valerolactone in the 13.8 to 340 K temperature range, Vysokomol. Soedin.,
Ser. A, 1982, 24, 568-574. [all data]
Evstopov, Lebedev, et al., 1981
Evstopov, A.A.; Lebedev, B.V.; Kulagina, T.G.; Lebedev, N.K.,
Thermodynamics of the polymerization process of d-valerolactone and poly-d-valerolactone in the range 0 to 350 K,
Termodin. Org. Soedin., 1981, 20-31. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Anonymous, 1955
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 45, Tech. Rep. 14, No. 1, Ohio State Univ., 1955. [all data]
Lebedev and Yevstropov, 1983, 2
Lebedev, B.V.; Yevstropov, A.A. (see evstro aa),
Thermodynamics of β-propiolactone, γ-butyrolactone, δ- valerolactone, and ε-caprolactone from 13.8 to 340 K,
J. Chem. Thermodyn., 1983, 15, 115. [all data]
Evstropov, Lebedev, et al., 1982
Evstropov, A.A.; Lebedev, B.V.; Kulagina, T.G.; Lebedev, N.K.,
Calorimetric study of γ-valerolactone, poly-γ-valerolactone and of the process of polymerization of γ-valerolactone in the 13.8 to 340 K temperature range,
Vysokomol. Soedin., Ser. A, 1982, 24, 568-574. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Schuette and Thomas, 1930
Schuette, H.A.; Thomas, Ralph W.,
NORMAL VALEROLACTONE. II. ITS VAPOR PRESSURE,
J. Am. Chem. Soc., 1930, 52, 5, 2028-2030, https://doi.org/10.1021/ja01368a046
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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