trans-Cinnamic acid
- Formula: C9H8O2
- Molecular weight: 148.1586
- IUPAC Standard InChI: InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
- IUPAC Standard InChIKey: WBYWAXJHAXSJNI-VOTSOKGWSA-N
- CAS Registry Number: 140-10-3
- 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. - Stereoisomers:
- Other names: 2-Propenoic acid, 3-phenyl-, (E)-; Cinnamic acid, (E)-; (E)-Cinnamic acid; trans-β-Carboxystyrene; trans-3-Phenyl-2-propenoic acid; trans-3-Phenylacrylic Acid; (E)-3-Phenyl-2-propenoic acid; (2E)-3-Phenyl-2-propenoic acid; (E)-3-Phenylacrylic acid; 2-Propenoic acid, 3-phenyl-, (2E)-; NSC 44010; Cinnamic acid
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Condensed phase thermochemistry data
Go To: Top, 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 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°solid | -325.3 | kJ/mol | Ccb | Zavoianu, Ciocazan, et al., 1990 | ALS |
| ΔfH°solid | -337.0 | kJ/mol | Ccb | Parks and Mosher, 1962 | ALS |
| ΔfH°solid | -340. | kJ/mol | Ccb | Landrieu, Baylocq, et al., 1929 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -4359.3 | kJ/mol | Ccb | Zavoianu, Ciocazan, et al., 1990 | Corresponding ΔfHºsolid = -326. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -4348. ± 2. | kJ/mol | Ccb | Parks and Mosher, 1962 | Corresponding ΔfHºsolid = -336.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -4344.7 | kJ/mol | Ccb | Landrieu, Baylocq, et al., 1929 | Corresponding ΔfHºsolid = -340. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 197.5 | 323. | Satoh and Sogabe, 1939 | T = 0 to 100°C. Mean value.; DH |
Phase change data
Go To: Top, 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 compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 573.2 | K | N/A | Weast and Grasselli, 1989 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 107.1 ± 0.8 | kJ/mol | ME | Monte and Hillesheim, 1999 | Based on data from 333. to 347. K.; AC |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 73.9 | 445. | A | Stephenson and Malanowski, 1987 | Based on data from 430. to 573. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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| Temperature (K) | A | B | C | Reference | Comment |
|---|---|---|---|---|---|
| 400.7 to 573. | 6.14389 | 3321.821 | -32.118 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 22.626 | 406.15 | N/A | Singh and Kumar, 1986 | DH |
| 22.21 | 406.1 | N/A | Mota, Queimada, et al., 2008 | AC |
| 22.6 | 404.8 | DSC | Sharma, Jamwal, et al., 2004 | AC |
| 22.63 | 406.2 | N/A | Acree, 1991 | AC |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Zavoianu, Ciocazan, et al., 1990
Zavoianu, D.; Ciocazan, I.; Moga-Gheorghe, S.; Bornaz, C.,
Structure and reactivity of acids. Heats of combustion and formation of some phenylacrylic acids.,
Rev. Chim. (Bucharest), 1990, 41, 234-236. [all data]
Parks and Mosher, 1962
Parks, G.S.; Mosher, H.P.,
Heats of combustion and formation of seven organic compounds containing oxygen,
J. Chem. Phys., 1962, 37, 919-920. [all data]
Landrieu, Baylocq, et al., 1929
Landrieu, P.; Baylocq, F.; Johnson, J.R.,
Etude thermochimique dans la serie furanique,
Bull. Soc. Chim. France, 1929, 45, 36-49. [all data]
Satoh and Sogabe, 1939
Satoh, S.; Sogabe, T.,
The specific heats of some solid aromatic acids and their ammonium salts and the atomic heat of nitrogen,
Sci. Pap. Inst. Phys. Chem. Res. (Tokyo), 1939, 36, 449-457. [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]
Monte and Hillesheim, 1999
Monte, Manuel J.S.; Hillesheim, Dorothea M.,
Vapour pressures, enthalpies and entropies of sublimation of trans -cinnamic acid and of nine methoxy and dimethoxycinnamic acids,
The Journal of Chemical Thermodynamics, 1999, 31, 11, 1443-1456, https://doi.org/10.1006/jcht.1999.0540
. [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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Singh and Kumar, 1986
Singh, N.B.; Kumar, P.,
Solidification behavior of the cinnamic acid-p-nitrophenol eutectic system,
J. Chem. Eng. Data, 1986, 31, 406-408. [all data]
Mota, Queimada, et al., 2008
Mota, Fatima L.; Queimada, Antonio J.; Pinho, Simao P.; Macedo, Eugenia A.,
Aqueous Solubility of Some Natural Phenolic Compounds,
Ind. Eng. Chem. Res., 2008, 47, 15, 5182-5189, https://doi.org/10.1021/ie071452o
. [all data]
Sharma, Jamwal, et al., 2004
Sharma, B.L.; Jamwal, R.; Kant, R.,
Thermodynamic and lamella models relationship for the eutectic system benzoic acid-- cinnamic acid,
Cryst. Res. Technol., 2004, 39, 5, 454-464, https://doi.org/10.1002/crat.200310210
. [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, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid Tboil Boiling point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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