Oxacyclotetradecan-2-one
- Formula: C13H24O2
- Molecular weight: 212.3285
- IUPAC Standard InChI: InChI=1S/C13H24O2/c14-13-11-9-7-5-3-1-2-4-6-8-10-12-15-13/h1-12H2
- IUPAC Standard InChIKey: IUDIJIVSWGWJNV-UHFFFAOYSA-N
- CAS Registry Number: 1725-04-8
- 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: Tridecanoic acid, 13-hydroxy-, μ-lactone; Tridecanolide; 1,13-Tridecanolide; 1-Oxacyclotetradecan-2-one; 13-Tridecanolide; Tridecano-13-lactone
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -136.0 ± 0.6 | kcal/mol | Cm | Wiberg and Waldron, 1991 | Heat of reduction, Hfusion=1.72 kcal/mol |
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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -154.0 ± 0.5 | kcal/mol | Cm | Wiberg and Waldron, 1991 | Heat of reduction, Hfusion=1.72 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔfH°solid | -154.9 ± 0.69 | kcal/mol | Ccb | Lebedev, Yevstropov, et al., 1981 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1887.0 ± 0.69 | kcal/mol | Ccb | Lebedev, Yevstropov, et al., 1981 | Corresponding ΔfHºsolid = -155.4 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 96.03 | cal/mol*K | N/A | Lebedev, Evstropov, et al., 1981 | DH |
| S°solid,1 bar | 96.06 | cal/mol*K | N/A | Lebedev, Yevstropov, et al., 1981, 2 | DH |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 95.20 | 298.15 | Lebedev, Evstropov, et al., 1981 | T = 5 to 400 K.; DH |
| 95.20 | 298.15 | Lebedev, Yevstropov, et al., 1981, 2 | T = 10.3 to 330 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Ttriple | 300.42 | K | N/A | Lebedev, Evstropov, et al., 1981, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC |
| Ttriple | 300.4 | K | N/A | Lebedev, Evstropov, et al., 1981, 3 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.1 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 17.9 | kcal/mol | N/A | Wiberg and Waldron, 1991 | DRB |
| ΔvapH° | 17.4 ± 0.41 | kcal/mol | MM | Wiberg and Waldron, 1991 | Based on data from 375. to 405. K.; AC |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 15.9 ± 0.26 | 390. | MM | Wiberg and Waldron, 1991 | Based on data from 375. to 405. K.; AC |
| 16.1 | 408. | A | Stephenson and Malanowski, 1987 | Based on data from 393. to 443. K.; AC |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 2.17 | 300.4 | Domalski and Hearing, 1996 | AC |
Enthalpy of phase transition
| ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 4.3380 | 290.63 | crystaline, II | crystaline, I | Lebedev, Evstropov, et al., 1981 | DH |
| 2.165 | 300.4 | crystaline, I | liquid | Lebedev, Evstropov, et al., 1981 | DH |
| 4.3380 | 290.63 | crystaline, II | crystaline, I | Lebedev, Yevstropov, et al., 1981, 2 | DH |
| 2.165 | 300.4 | crystaline, I | liquid | Lebedev, Yevstropov, et al., 1981, 2 | DH |
Entropy of phase transition
| ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 14.93 | 290.63 | crystaline, II | crystaline, I | Lebedev, Evstropov, et al., 1981 | DH |
| 7.22 | 300.4 | crystaline, I | liquid | Lebedev, Evstropov, et al., 1981 | DH |
| 14.9 | 290.63 | crystaline, II | crystaline, I | Lebedev, Yevstropov, et al., 1981, 2 | DH |
| 7.22 | 300.4 | crystaline, I | liquid | Lebedev, Yevstropov, et al., 1981, 2 | DH |
Mass spectrum (electron ionization)
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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 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 | W. KELLY UNILEVER RESEARCH COLWORTH/WELWYN, BEDFORD U.K. |
| NIST MS number | 9818 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 | 1627. | Lopes, Strobl, et al., 2004 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 260. C |
Kovats' RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 2030. | Lopes, Strobl, et al., 2004 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 5. min, 3. K/min; Tend: 220. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5MS | 1640.8 | Andriamaharavo, 2014 | 30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min) |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SPB-5 | 1636. | Doneanu and Anitescu, 1998 | 50. m/0.32 mm/0.25 μm, He, 3. K/min, 240. C @ 20. min; Tstart: 60. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | CP Sil 8 CB | 1590. | Nivinskienë, Butkienë, et al., 2005 | 50. m/0.32 mm/0.25 μm, He; Program: 60C(1min) => 5C/min => 160C => 5C/min => 250C(3min) |
Normal alkane RI, polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-Innowax | 2082. | Paroul, Rota, et al., 2002 | 30. m/0.32 mm/0.5 μm, H2; Program: 40C (8min) => 3C/min => 180C => 20C/min => 240C |
| Capillary | FFAP | 2062. | Reddy, Angers, et al., 1998 | 25. m/0.2 mm/0.33 μm, H2; Program: 40C(5min) => 4C/min => 170C => 8C/min => 240C (12min) |
| Capillary | NB-351 | 2055. | Kerrola and Kallio, 1994 | 25. m/0.32 mm/0.2 μm, He; Program: 35C(5min) => 2.5C/min => 150C => 5C/min => 240C (20min) |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, 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]
Lebedev, Yevstropov, et al., 1981
Lebedev, B.V.; Yevstropov, A.A.; Kiparisova, Ye.G.,
Thermodynamics of undecanolactone, tridecanolactone, and pentadecanolactone from 0 to 340 K,
J. Chem. Thermodyn., 1981, 13, 1185-1204. [all data]
Lebedev, Evstropov, et al., 1981
Lebedev, B.V.; Evstropov, A.A.; Kiparisova, Y.G.; Sheveleva, N.P.,
Thermodynamics of tridecanolactone, its polymerization process, and the resultant poly(tridecanolactone) in the 0-430 K range,
Vysokomol. Soedin., 1981, B23, 551-554. [all data]
Lebedev, Yevstropov, et al., 1981, 2
Lebedev, B.V.; Yevstropov, A.A.; Kiparisova, Y.G.,
Thermodynamic properties of undecanolactone over the range, 1981, Termodin. [all data]
Lebedev, Evstropov, et al., 1981, 2
Lebedev, B.V.; Evstropov, A.A.; Kiparisova, Ye.G.,
Thermodynamics of undecanolactone, tridecanolactone, and pentadecanolactone from 0 to 340 K,
J. Chem. Thermodyn., 1981, 13, 1185. [all data]
Lebedev, Evstropov, et al., 1981, 3
Lebedev, B.V.; Evstropov, A.A.; Kiparisova, E.G.; Sheveleva, N.P.,
Thermodynamics of Tridecanolactone, Its Polymerization Process, and the Resultant Poly(tridecanolactone) in the 0 - 430 K Range,
Vysokomol. Soedin, Ser. B, 1981, 24, 551-4. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [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]
Lopes, Strobl, et al., 2004
Lopes, D.; Strobl, H.; Kolodziejczyk, P.,
14-Methylpentadecano-15-lactone (Muscolide): a new macrocyclic lactone from the oil of Angelica archangelica L.,
Chemistry and Biodiversity, 2004, 1, 12, 1880-1887, https://doi.org/10.1002/cbdv.200490144
. [all data]
Andriamaharavo, 2014
Andriamaharavo, N.R.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]
Doneanu and Anitescu, 1998
Doneanu, C.; Anitescu, G.,
Supercritical carbon dioxide extraction of Angelica archangelica L. root oil,
J. Supercrit. Fluids, 1998, 12, 1, 59-67, https://doi.org/10.1016/S0896-8446(97)00040-5
. [all data]
Nivinskienë, Butkienë, et al., 2005
Nivinskienë, O.; Butkienë, R.; Mockutë, D.,
Chemical composition of seed (fruit) essential oils of Angelica archangelica L. growing wild in Lithuania,
Chemija, 2005, 16, 3-4, 51-54. [all data]
Paroul, Rota, et al., 2002
Paroul, N.; Rota, L.; Frizzo, C.; Atti dos Santos, A.C.; Moyna, P.; Gower, A.E.; Serafini, L.A.,
Chemical composition of the volatiles of Angelica root obtained by hydrodistillation and supercritical CO2 extraction,
J. Essent. Oil Res., 2002, 14, 4, 282-285, https://doi.org/10.1080/10412905.2002.9699855
. [all data]
Reddy, Angers, et al., 1998
Reddy, M.V.B.; Angers, P.; Gosselin, A.; Arul, J.,
Characterization and use of essential oil from Thymus vulgaris against Botrytis cinerea and Rhizopus stolonifer in strawberry fruits,
Phytochemistry, 1998, 47, 8, 1515-1520, https://doi.org/10.1016/S0031-9422(97)00795-4
. [all data]
Kerrola and Kallio, 1994
Kerrola, K.M.; Kallio, H.P.,
Extraction of volatile compounds of angelica (Angelica archangelica L.) root by liquid carbon dioxide,
J. Agric. Food Chem., 1994, 42, 10, 2235-2245, https://doi.org/10.1021/jf00046a030
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfH°solid Enthalpy of formation of solid 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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