Coumarin

• Formula: C₉H₆O₂
• Molecular weight: 146.1427
• IUPAC Standard InChI: InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H Copy

  
• IUPAC Standard InChIKey: ZYGHJZDHTFUPRJ-UHFFFAOYSA-N Copy
• CAS Registry Number: 91-64-5
• 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.
• Isotopologues:
  • Coumarin-d6
• Other names: 2H-1-Benzopyran-2-one; cis-o-Coumarinic acid lactone; o-Hydroxycinnamic acid lactone; Benzo-α-pyrone; Coumarinic anhydride; Rattex; Tonka bean camphor; 1,2-Benzopyrone; 2-Propenoic acid, 3-(2-hydroxyphenyl)-, δ-lactone; 2H-Benzo[b]pyran-2-one; o-Hydroxycinnamic lactone; Cinnamic acid, o-hydroxy-, δ-lactone; Cumarin; 2-Oxo-1,2-benzopyran; 2H-1-Benzopyran, 2-oxo-; o-Hydroxyzimtsaure-lacton; Kumarin; NCI C07103; NSC 8774; 2H-Chromen-2-one
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas Chromatography
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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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
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

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of sublimation

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 as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Appearance energy determinations

IR 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: Coblentz Society, Inc.

Condensed Phase Spectrum

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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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

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

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Watik and Sabbah, 1991
Watik, L.E.; Sabbah, R., Etude thermodynamique de la coumarine et de l'anthrone, Bull. Soc. Chim. Fr., 1991, 128, 344-349. [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]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Serpinskii, Voitkevich, et al., 1958
Serpinskii, V.V.; Voitkevich, S.A.; Lyuboshits, N.Yu., Trudy Vsesoyuz. Nauch.-Issledovatel. Inst. Sintet. I. Natural. Dushistykh Veshchestv, 1958, 4, 125. [all data]

Sorum and Durand, 1952
Sorum, C.H.; Durand, E.A., The Melting of Binary Eutectics, J. Am. Chem. Soc., 1952, 74, 1071. [all data]

Matos, Sousa, et al., 2009
Matos, M. Agostinha R.; Sousa, Clara C.S.; Miranda, Margarida S.; Morais, Victor M.F.; Liebman, Joel F., Energetics of Coumarin and Chromone, J. Phys. Chem. B, 2009, 113, 32, 11216-11221, https://doi.org/10.1021/jp9026942 . [all data]

El Watik and Sabbah, 1991
El Watik, L.; Sabbah, R., Thermodynamic study of coumarin and anthrone, Bull. Soc. Chim. Fr., 1991, 344. [all data]

Sabbah and Watik, 1992
Sabbah, R.; Watik, L. El, Thermodynamic study of anthrone, coumarin and phenazine, Journal of Thermal Analysis, 1992, 38, 4, 803-809, https://doi.org/10.1007/BF01979412 . [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]

Sabbah and El Watik, 1992
Sabbah, R.; El Watik, L., Thermodynamic study of anthrone, counmarin and phenazine, J. Therm. Anal., 1992, 38, 803-809. [all data]

Serpinskii, Voitkevich, et al., 1953
Serpinskii, V.V.; Voitkevich, S.A.; Lyuboshits, N.Y., Zh. Fiz. Khim., 1953, 27, 1032. [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

El Watik and Sabbah, 1991, 2
El Watik, L.; Sabbah, R., Thermodynamic study of coumarin and anthrone, Bull. Soc. Chim. France, 1991, 128, 344-349. [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]

Redchenko, Safronov, et al., 1992
Redchenko, V.V.; Safronov, A.I.; Kirpichenok, M.A.; Grandberg, I.I.; Traven', V.F., Electronic structure of π-systems. XV. Photoelectron spectra of 7-aminocoumarin derivatives, J. Gen. Chem. USSR, 1992, 62, 2313. [all data]

Occolowitz and White, 1968
Occolowitz, J.L.; White, G.L., Energetic considerations in the assignment of some fragment ion structures, Australian J. Chem., 1968, 21, 997. [all data]

Tang, McGowan, et al., 1979
Tang, S.-Y.; McGowan, J.C.; Singh, M.; Galatsis, P.; Ellis, B.E.; Boyd, R.K.; Brown, S.A., Mass spectrometry of some furanocoumarins, Can. J. Chem., 1979, 57, 1995. [all data]

Barnes and Occolowitz, 1964
Barnes, C.S.; Occolowitz, J.L., The mass spectra of some naturally occurring oxygen heterocycles and related compounds, Australian J. Chem., 1964, 17, 975. [all data]

Ikawa and Link., 1950
Ikawa, M.; Link., K.P., J. Am. Chem. Soc., 1950, 72, 4373. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References

• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  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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