Azulene

• Formula: C₁₀H₈
• Molecular weight: 128.1705
• IUPAC Standard InChI: InChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H Copy

  
• IUPAC Standard InChIKey: CUFNKYGDVFVPHO-UHFFFAOYSA-N Copy
• CAS Registry Number: 275-51-4
• 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: Bicyclo[5.3.0]decapentaene; Cyclopentacycloheptene; Azunamic; Bicyclo(5.3.0)-1,3,5,7,9-decapentaene; Bicyclo(0.3.5)deca-1,3,5,7,9-pentaene; BICYCLO(5.3.0)-DECA-2,4,6,8,10-PENTAENE; Azusalen [as sodium sulfonate]
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • Gas Phase Kinetics Database
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

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.

Enthalpy of vaporization

Enthalpy of sublimation

Enthalpy of fusion

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Phase change data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Gas Chromatography

Go To: Top, Gas 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, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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Lee's RI, non-polar column, temperature ramp

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References

Go To: Top, Gas 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.

Roth, Bohm, et al., 1983
Roth, W.R.; Bohm, M.; Lenhartz, H-W.; Vogel, E., Heats of hydrogenation. Part 5. Resonance energy of bridged [10]annulenes, Angew. Chem., 1983, 95, 1011-1012. [all data]

Kovats, Gunthard, et al., 1957
Kovats, E.; Gunthard, H.; Plattner, A., Die tabellen 4 und 5 enthalten numerische fehler und lanten richtig, Helv. Chim. Acta, 1957, 40, 000. [all data]

Kovats, Gunthard, et al., 1955
Kovats, E.; Gunthard, Hs.H.; Plattner, Pl.A., Thermische eigenschaften von azulenen, Helv. Chim. Acta, 1955, 38, 1912-1919. [all data]

Kovats E., 1955
Kovats E., Thermochemical properties of azulene, Helv. Chim. Acta, 1955, 38, 1912-1919. [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]

Turner, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Doering, W. vonE.; Knox, L.H.; Mayer, J.R.; Wiley, D.W., Heats of Hydrogenation III. Hydrogenation of Cyclooctatetraene and of Some Seven-membered Non-benzenoid Aromatic Compounds, J. Am. Chem. Soc., 1957, 79, 4127. [all data]

Birrrell, 1935
Birrrell, K.S., Studies in the Chemistry of Azulene, J. Am. Chem. Soc., 1935, 57, 893. [all data]

Chickos, Hesse, et al., 1998
Chickos, James; Hesse, Donald; Hosseini, Sarah; Nichols, Gary; Webb, Paul, Sublimation enthalpies at 298.15K using correlation gas chromatography and differential scanning calorimetry measurements, Thermochimica Acta, 1998, 313, 2, 101-110, https://doi.org/10.1016/S0040-6031(97)00432-2 . [all data]

Bauder and Gunthard, 1962
Bauder, A.; Gunthard, H.Hs., 196. Dampfdruck von azulen, Helv. Chim. Acta, 1962, 62, 1698. [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]

Meyer and Gens, 1977
Meyer, Edwin F.; Gens, Timothy H., Vapor pressure of azulene between 114 and 261.degree.C, J. Chem. Eng. Data, 1977, 22, 1, 30-31, https://doi.org/10.1021/je60072a019 . [all data]

Bauder and G«65533»nthard, 1962
Bauder, A.; G«65533»nthard, Hs.H., Dampfdruck von Azulen, Helv. Chim. Acta, 1962, 45, 5, 1698-1702, https://doi.org/10.1002/hlca.19620450536 . [all data]

Hoyer and Peperle, 1958
Hoyer, H.; Peperle, W., Z. Elektrochem., 1958, 62, 61. [all data]

Dallos, Sisak, et al., 2000
Dallos, A.; Sisak, A.; Kulcsár, Z.; Kováts, E., Pair-wise interactions by gas chromatography VII. Interaction free enthalpies of solutes with secondary alcohol groups, J. Chromatogr. A, 2000, 904, 2, 211-242, https://doi.org/10.1016/S0021-9673(00)00908-0 . [all data]

Reddy, Dutoit, et al., 1992
Reddy, K.S.; Dutoit, J.-Cl.; Kovats, E. sz., Pair-wise interactions by gas chromatography. I. Interaction free enthalpies of solutes with non-associated primary alcohol groups, J. Chromatogr., 1992, 609, 1-2, 229-259, https://doi.org/10.1016/0021-9673(92)80167-S . [all data]

Engewald, Wennrich, et al., 1979
Engewald, W.; Wennrich, L.; Ritter, E., Molekülstruktur und Retentionsverhalten. XII. Zur Retention von Alkylnaphthalinen Bei der Gasverteilungs- und Gas-Adsorptions-Chromatographie, J. Chromatogr., 1979, 174, 2, 315-323, https://doi.org/10.1016/S0021-9673(00)86005-7 . [all data]

Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E., Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603 . [all data]

Carugno and Rossi, 1967
Carugno, N.; Rossi, S., Evaluation of polynuclear hydrocarbons in cigarette smoke by glass capillary columns, J. Gas Chromatogr., 1967, 5, 2, 103-106, https://doi.org/10.1093/chromsci/5.2.103 . [all data]

Shimoda, Wu, et al., 1996
Shimoda, M.; Wu, Y.; Osajima, Y., Aroma compounds from aqueous solution of Haze (Rhus succedanea) honey determined by adsorptive column chromatography, J. Agric. Food Chem., 1996, 44, 12, 3913-3918, https://doi.org/10.1021/jf9601168 . [all data]

Nadim, Malik, et al., 2011
Nadim, M.M.; Malik, A.A.; Ahmad, J.; Bakshi, S.K., The essential oil composition of Achillea millefolium L. cultivated under tropical conditions in India, World J. Agricultural Sci., 2011, 7, 5, 561-565. [all data]

Piyachaiseth, Jirapakkul, et al., 2011
Piyachaiseth, T.; Jirapakkul, W.; Chaiseri, S., Aroma compounds of flash-fried rice, Kasetsart J. (Nat. Sci.), 2011, 45, 717-729. [all data]

Kaypak and Avsar, 2008
Kaypak, D.; Avsar, Y.K., Volatile and odor-active compounds of tuzlu yoghurt, Asian J. Chem., 2008, 20, 5, 3641-3648. [all data]

Lee and Kim, 2002
Lee, D.-S.; Kim, N.-S., Identification of fragrances from chestnut blossom by gas chromatography-ion trap mass spectrometry, Bull. Korean Chem. Soc., 2002, 23, 11, 1647-1650, https://doi.org/10.5012/bkcs.2002.23.11.1647 . [all data]

Vernin, 1991
Vernin, G., Volatile constituents of the essential oil of Santolina chamaecyparissus L., J. Essent. Oil Res., 1991, 3, 1, 49-53, https://doi.org/10.1080/10412905.1991.9697907 . [all data]

Lee, Vassilaros, et al., 1979
Lee, M.L.; Vassilaros, D.L.; White, C.M.; Novotny, M., Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons, Anal. Chem., 1979, 51, 6, 768-773, https://doi.org/10.1021/ac50042a043 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  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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