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
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• 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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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

Reaction 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₁₀H₇^- +  =

By formula: C₁₀H₇^- + H⁺ = C₁₀H₈

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₁₀H₈ = (C₆H₇N⁺ • C₁₀H₈)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

5 +  =

By formula: 5H₂ + C₁₀H₈ = C₁₀H₁₈

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.

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]

Meot-ner, Liebman, et al., 1988
Meot-ner, M.; Liebman, J.F.; Kafafi, S.A., Ionic Probes of Aromaticity in Annelated Rings, J. Am. Chem. Soc., 1988, 110, 18, 5937, https://doi.org/10.1021/ja00226a001 . [all data]

Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [all data]

Turner, Meador, et al., 1957, 2
Turner, R.B.; Meador, W.R.; Doering, W.E.; Knox, L.H.; Mayer, J.R.; Wiley, D.W., Heats of hydrogenation. III. Hydrogenation of cycllooctatetraene and of some seven-membered non-benzenoid aromatic compounds, J. Am. Chem. Soc., 1957, 79, 4127-4133. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  T	Temperature
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  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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