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+ Copy

  
• IUPAC Standard InChIKey: WBYWAXJHAXSJNI-VOTSOKGWSA-N Copy
• 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:
  • (Z)-3-Phenyl-2-propenoic acid
  • 2-Propenoic acid, 3-phenyl-
• 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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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

Constant pressure heat capacity of solid

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:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Enthalpy of fusion

Gas phase ion energetics 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 by: Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

Ionization energy determinations

UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, UV/Visible spectrum, 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]

Schaldach, 1984
Schaldach, B., Chemistry of gaseous ions. Part VIII. Bond strength and mass spectrometric fragmentation of 2-methoxycinnamic acid, Int. J. Mass Spectrom. Ion Processes, 1984, 56, 237. [all data]

Wawzonek and Lyons, 1950
Wawzonek, S.; Lyons, P., J. Org. Chem., 1950, 15, 593. [all data]

Notes

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• 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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